Benzenesulfonamides as herbicides

ABSTRACT

This invention relates to ortho-heterocyclicbenzenesulfonylureas and, more particularly, to ortho-furanylbenzenesulfonylureas, ortho-thienylbenzenesulfonylureas or ortho-pyrrolylbenzenesulfonylureas and their use in agriculturally suitable compositions as pre-emergence and/or post-emergence herbicides and as plant growth regulants.

RELATED APPLICATION

This application is a divisional of my copending application U.S. Ser.No. 437,637 filed Nov. 1, 1982, now U.S. Pat. No. 4,460,401 which is acontinuation-in-part of my copending application U.S. Ser. No. 337,933,filed Jan. 7, 1982 now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to ortho-heterocyclicbenzensulfonylureas and,more particularly, to orthofuranylbenzenesulfonylureas,ortho-thienylbenzenesulfonylureas or ortho-pyrrolylbenzenesulfonylureasand their use in agriculturally suitable compositions as pre-emergenceand/or post-emergence herbicides and as plant growth regulants.

DESCRIPTION OF THE PRIOR ART

U.S. Pat. Nos. 4,127,405 and 4,169,719 disclose a broad class ofpyrimidine and triazine sulfonylurea compounds.

European Pat. No. 7687 discloses herbicidal sulfonylurea compounds suchas, among others, ##STR1## where X is CH₃ or OCH₃ ;

Z is CH or N; and

Y is C₁ -C₄ alkyl substituted with OCH₃, OC₂ H₅, CN, C(O)L, or 1-3 atomsof F, Cl, or Br, where L is NH₂, OH, N(OCH₃)CH₃, NH(C₁ -C₄ alkyl), N(C₁-C₄ alkyl) or C₁ -C₆ alkoxy.

U.S. Ser. No. 264,331 discloses herbicidal o-phenylbenzenesulfonylureas.

SUMMARY OF THE INVENTION

This invention relates to compounds of Formula I, suitable agriculturalcompositions containing them, and their method of use as general and/orselective preemergence and/or postemergence herbicides and as plantgrowth regulants. ##STR2## where Q is ##STR3## where W is O or S;

W' is O or S;

R₁ is H, F, Cl, Br, CH₃, CF₃ or OCH₃ ;

R₃ is H, CH₃, C₂ H₅, Cl, Br, OCH₃ or OC₂ H₅ ;

R₅ is H, CH₃, C₂ H₅, Cl, Br, OCH₃ or OC₂ H₅ ;

R₁₇ is H, CH₃, C₂ H₅, Cl, Br, OCH₃, OC₂ H₅ or CO₂ CH₃ ;

R₁₂ is H or CH₃ ;

R₁₂ ' is H or CH₃ ;

R₁₃ is H or CH₃ ;

R₁₈ is H or CH₃ ;

R₁₉ is H or CH₃ ;

R₂₀ is H or CH₃ ;

R₂₁ is H or CH₃ ;

R₂₂ is H or CH₃ ;

R₂₃ is H or CH₃ ; ##STR4## X is CH₃, OCH₃ or Cl; Y is CH₃, C₂ H₅, CH₂OCH₃, OCH₃, OC₂ H₅, CH(OCH₃)₂, SCH₃, CF₃, NH₂, NHCH₃, N(CH₃)₂, OCH₂ CH₂OCH₃, OCH₂ CF₃ or ##STR5## Z is CH or N; X₁ is CH₃, OCH₃ or Cl;

G is O or CH₂ ;

X₂ is C₁ -C₃ alkyl or CH₂ CF₃ ;

Y₂ is CH₃ O, C₂ H₅ O, CH₃ S or C₂ H₅ S;

and their agriculturally suitable salts; provided that

(1) when W is S, then R₁₃ is H, ##STR6## Y is CH₃, OCH₃, C₂ H₅, CH₂OCH₃, ##STR7## (2) when Q is ##STR8## then R₃ is H, CH₃ or C₂ H₅ ; R₅ isH, CH₃ or C₂ H₅ ; and R₁₇ is H, CH₃, C₂ H₅ or --CO₂ CH₃ ;

(3) when one of R₃, R₅, R₁₇ is other than H, then the other twosubstituents are H or CH₃ ;

(4) the total number of carbon atoms in R₁₂, R₁₂ ', R₁₈, R₁₉, R₂₀, R₂₁,R₂₂ and R₂₃ is less than or equal to 4;

(5) when X is Cl, then Z is CH and Y is OCH₃, NH₂, OC₂ H₅, NHCH₃ orN(CH₃)₂.

Preferred for their higher herbicidal activity and/or their morefavorable ease of synthesis are:

(1) Compounds of Formula I where W is O;

(2) Compounds of Preferred (1) where R₁ and R₁₃ are H;

(3) Compounds of Preferred (2) where R₃ is H, CH₃ or C₂ H₅ ; R₅ is H,CH₃ or C₂ H₅ ; and R₁₇ is H, CH₃, C₂ H₅ or --CO₂ CH₃ ;

(4) Compounds of Preferred (3) where Y is CH₃, CH₂ OCH₃, OCH₃, OC₂ H₅,CH(OCH₃)₂ or ##STR9## (5) Compounds of Preferred (4) where Q is##STR10## (6) Compounds of Preferred (4) where Q is ##STR11## (7)Compounds of Preferred (4) where Q is ##STR12## (8) Compounds ofPreferred (4) where Q is ##STR13## (9) Compounds of Preferred (4) whereQ is ##STR14## (10) Compounds of Preferred (4) where Q is ##STR15## (11)Compounds of Preferred (4) where Q is ##STR16## (12) Compounds ofPreferred (4) where Q is ##STR17## (13) Compounds of Preferred (4) whereQ is ##STR18## (14) Compounds of Preferred (4) where Q is ##STR19## (15)Compounds of Preferred (4) where Q is ##STR20## (16) Compounds ofPreferred (4) where Q is ##STR21## (17) Compounds of Preferred (4) whereQ is ##STR22## (18) Compounds of Preferred (4) where Q is ##STR23## (19)Compounds of Preferred (4) where Q ##STR24## (20) Compounds of Preferred(4) where Q ##STR25## and (21) Compounds of Preferred (4) where Q##STR26##

Specifically Preferred for reasons of their highest herbicidal activityor most favorable ease of synthesis are:

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide;

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide;

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide;

N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide;

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide;and

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(tetrahydrofuran-2-yl)benzenesulfonamide.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The ortho-heterocyclicbenzenesulfonylureas of Formula I can be preparedby reacting the appropriately substituted benzenesulfonamide II with anappropriate methyl heteroaryl carbamate III in the presence of anequimolar amount of trimethylaluminum according to the procedure ofEquation 1. Unless indicated otherwise, all temperatures are in °C.##STR27## wherein R₁, R₁₃, Q and A are as previously defined, and W isO.

The reaction of Equation 1 is best carried out in methylene chloride at25° to 40° C. for 24 to 96 hours under a nitrogen atmosphere. Theproduct can be isolated by the addition of an aqueous acetic acidsolution followed by extraction of the product into methylene chlorideor direct filtration of a product of low solubility. The product canordinarily be purified by trituration with solvents such as n-butylchloride or ether or by column chromatography.

Further details of this reaction and the preparation of the carbamatesof Formula III can be found in U.S. Ser. No. 337,934.

Compounds of Formula I, in which Q does not include Q-3, Q-4 or Q-5, mayalso be prepared by reacting the appropriately substitutedbenzenesulfonyl isocyanate or isothiocyanate with an appropriateaminoheterocycle, V, as shown in Equation 2. ##STR28## wherein R₁, R₁₃,W and A are as previously defined, and Q is Q-1, Q-2, and Q-6 to Q-11.

The reaction of Equation 2 can best be carried out in an inert aproticsolvent such as methylene chloride, tetrahydrofuran or acetonitrile at atemperature between 20° and 80°. A catalytic amount of1,4-diazabicyclo[2,2,2]octane (DABCO) may be used to accelerate thereaction. In cases in which the products are insoluble in the reactionsolvent, they may be isolated by simple filtration. When the productsare soluble, they may be isolated by evaporation of the solvent andtrituration of the residue with solvents such as 1-chlorobutane, ethylether or methanol and filtration.

The benzenesulfonyl isocyanates of Formula IVa may be prepared as shownbelow in Equation 3, by phosgenation of the sulfonamide II in thepresence of butyl isocyanate. The sulfonyl isocyanates of Formula IV mayalso be prepared, as shown in Equation 4, by phosgenation of the butylureas of Formula VI. ##STR29## wherein R₁ and Q are as defined inEquation 2.

The above reaction can be carried out by heating a mixture of theappropriate sulfonamide (II), an alkyl isocyanate such as butylisocyanate and a catalytic amount of a tertiary amine such as1,4-diaza[2,2,2]bicyclooctane (DABCO) in xylene, or other inert solventof boiling point ≦135° to approximately 135° C. Phosgene can then beadded to the mixture over a 1-6 hour period until an excess of phosgeneis present as indicated by a drop in the boiling point to less than 130°C. The mixture is then cooled and filtered to remove a small amount ofinsoluble byproducts. The solvent and the alkyl isocyanate can bedistilled off in vacuo leaving a residue of the crude sulfonylisocyanate, IVa, which can be used without further purification.##STR30## wherein R₁ and Q are as defined in Equation 2.

The compounds of Formula VI can be prepared by stirring a mixture of thesulfonamides, II, anhydrous potassium carbonate, and n-butyl isocyanatein acetone or methyl ethyl ketone at 25°-80° until all of thesulfonamide has reacted. The products can be isolated by quenching indilute mineral acid and recrystallizing the solid product. The compoundsVI are then treated with phosgene and a catalytic amount of DABCO inrefluxing xylene or chlorobenzene in a manner analogous to thatdescribed in Equation 3.

Sulfonylisothiocyanates of Formula I where W=S can be prepared bytreatment of sulfonamides with carbon disulfide and potassium hydroxidefollowed by the reaction of the dipotassium salt with phosgene accordingto the teaching of K. Hartke, Arch. Pharm., 299, 174 (1966).

Alternatively, compounds of Formula Ib in which W is S may be preparedby the reaction of the appropriate sulfonamide of Formula II with aheterocyclic isothiocyanate of Formula Va as depicted in Equation 5.##STR31## wherein A, Q and R₁ are as previously defined.

The reaction of Equation 5 is best carried out by dissolving orsuspending the sulfonamide and isothiocyanate in a polar solvent such asacetone, acetonitrile, ethyl acetate or methyl ethyl ketone, adding anequivalent of a base such as potassium carbonate and stirring themixture at ambient temperature up to the reflux temperature for one totwenty-four hours. In some cases, the product precipitates from thereaction mixture and can be removed by filtration. The product isstirred in dilute mineral acid, filtered and washed with cold water. Ifthe product does not precipitate from the reaction mixture it can beisolated by evaporation of the solvent, trituration of the residue withdilute mineral acid and filtering off the insoluble product.

The heterocyclic isothiocyanates which are used in the procedure ofEquation 5 are prepared, for example, according to the method of Japanpatent Application Pub: Kokai No. 51-143686, June 5, 1976, or that of W.Abraham and G. Barnikow, Tetrahedron, 29, 691-7 (1973).

The synthesis of heterocyclic amine derivatives such as those depictedby Formula V has been reviewed in "The Chemistry of HeterocyclicCompounds", a series published by Interscience Publ., New York andLondon, and the teachings of which are incorporated herein by reference.Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol.XVI of the above series.

The 5,6-dihydrofuro[2,3-d]pyrimidin-2-amines, thecyclopenta[d]pyrimidin-2-amines, and the6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-amines, are prepared asdescribed in unexamined European Patent Application No. 15,683.Synthesis of the furo[2,3-d]pyrimidin-2-amines are described inunexamined European Patent Application No. 46,677. The heterocyclicamines in which A is a triazole ring are disclosed in copending U.S.Application Ser. No. 382,711. Pyrimidine and triazine amines in which Yis dimethoxymethyl or 1,3-dioxolan-2-yl are prepared as described incopending U.S. Application Ser. No. 328,098.

Sulfonamides of Formula II, in which Q is Q-1 or Q-2, can be prepared bythe sequence of reactions shown in Equation 6. ##STR32## wherein R₁ andW' are as previously defined;

X' is Cl, Br or HSO₄ ;

R₃ and R₅ are H, CH₃ or C₂ H₅ ; and

R₁₇ is H, CH₃, C₂ H₅ or CO₂ CH₃.

Reaction (6a)

In this reaction an o-nitrosubstituted phenyl diazonium halide orsulfate is coupled with an appropriately substituted thiophene or furanin the presence of a catalyst such as cupric chloride. The conditionsnecessary for this transformation are described in Gomberg and Bachmann,J. Am. Chem. Soc., 46, 2339 (1924); J. Johnson, J. Chem. Soc., 895(1946); and in J. Pharm. Soc. (Japan), 90, 1150-1155 (1970). In caseswhere both the α- and the β-position of the thiophene or furan areavailable for coupling, both isomers are usually obtained with theα-coupled product being the predominent isomer. These isomers can beseparated by fractional crystallization or chromatography and carried onthrough the remaining three reactions of Equation 6.

Reaction (6b)

The reduction described in step (6b) is accomplished by treating asolution of the compounds of Formula IX, in a solvent such as ethanol,ethyl acetate, or DMF, in a pressure vessel, with 100-1000 pounds persquare inch of hydrogen at 80°-150° in the presence of a hydrogenationcatalyst such as 5-10% palladium absorbed on carbon. When thetheoretical amount of hydrogen has been absorbed, the solution is thencooled and the catalyst is removed by filtration. The product is thenisolated by evaporation of the solvent.

Reaction (6c)

The diazotization and coupling with sulfur dioxide, described in step6c, is accomplished in the following manner. A solution of the anilineof Formula X in a mixture of concentrated hydrochloric acid and glacialacetic acid is treated with a solution of sodium nitrite in water at -5°to 0° C. After stirring for 10-15 minutes at 0° C. to insure completediazotization, this solution is added to a mixture of an excess ofsulfur dioxide, and a catalytic amount of cuprous chloride in glacialacetic acid at 0°-5°. The temperature is kept at 0°-5° for 1/4 to 1 hourthen raised to 20°-25° and held at that temperature for 2-4 hours. Thissolution is then poured into a large excess of ice water, and thesulfonyl chloride products, XI, is isolated by filtration or byextraction into a solvent such as ethyl ether or methylene chloridefollowed by evaporation of the solvent.

Reaction (6d)

The amination described in step (6d) is carried out by treating asolution of the sulfonyl chloride of Formula XI with an excess ofanhydrous ammonia in a solvent such as ethyl ether or methylene chlorideat 0°-25° C. If the product sulfonamide, II, is insoluble, it may beisolated by filtration followed by washing out the salts with water. Ifthe product sulfonamide is soluble in the reaction solution, it may beisolated by filtering off the precipitated ammonium chloride andevaporation of the solvent.

Sulfonamides of Formula IIa can be chlorinated or brominated on thethiophene or furan ring by procedures well known in the art. Thesehalogenated sulfonamides may then be reacted with sodium methoxide inmethanol or sodium ethoxide in ethanol to replace the halogen atom witha methoxy or ethoxy group.

Alternatively, the substituted nitrobenzenes of Formula IX can beprepared by the procedure shown in Equation 7. ##STR33## wherein R₁, R₃,R₅, R₁₇, and W' are as previously defined.

In the reaction shown in Equation 7, a furyl- or thienyl copper compoundof Formula XII is reacted with an iodonitrobenzene in a solvent such aspyridine or quinoline. The copper compounds of Formula XII are preparedby reacting the corresponding lithium compounds with cuprous iodide orcuprous bromide in a solvent such as diethyl ether. The detailedprocedures for these types of reactions are described in the followingreferences: M. Nilsson and C. Ullenius, Acta. Chem. Scand., 24,2379-2388 (1970); C. Ullenius, Acta. Chem. Scand., 26, 3383-3386 (1972).

Sulfonamides containing a tetrahydrofuran or tetrahydrothiophene group(Formula II, Q=Q-6 and Q-7) can be prepared by catalytic reduction ofthe corresponding furan or thiophene compounds as shown in Equation 8.##STR34## wherein R₁, R₁₂, R₁₈, R₂₀, and W' are as previously defined.

Selective reductions of the type shown in Equation 8 are well known inthe literature. The choice of catalyst, solvent, pressure andtemperature for reduction of furans has been reviewed by Samuel Sevadeshin The Furans by A. P. Dunlop and F. N. Peters, Reinhold PublishingCorporation, New York, N.Y. 1953, pp. 674-713; and by P. N. Rylander inCatalytic Hydrogenation in Organic Synthesis, Academic Press, 1979, pp.227-234. The reduction of thiophenes is reviewed by H. D. Hartough inThiophene and Its Derivatives, The Chemistry of Heterocyclic CompoundsSeries, Interscience Publishers, Inc., New York, N.Y. 1952, pp. 167-169.

Sulfonamides containing a tetrahydrothiophene or tetrahydrothiopyrangroup can also be prepared by the sequence of reactions shown inEquation 9. ##STR35## wherein A' is ##STR36## R₁, R₁₂, R₁₂ ', R₁₈, R₁₉,R₂₀, R₂₁, R₂₂ and R₂₃ are as previously defined.

The general conditions used to carry out the reactions described inReactions (9a) and (9b) are described by P. G. Gassman and G. D.Gruetzmacher, J. Am. Chem. Soc., 96, 5487-5495 (1974). The proceduresshown in Reactions (9c) and (9d) are directly analogous to thosedescribed in Reactions (6c) and (6d).

Other sulfonamides containing tetrahydrofuran or tetrahydropyran groupscan be prepared by the sequence of reactions shown in Equation 10.##STR37## wherein A', R₁, R₁₂, R₁₂ ', R₁₈, R₁₉, R₂₀, R₂₁, R₂₂ and R₂₃are as previously defined; and

X" is Cl or Br.

Reaction (10a)

In this reaction a tert-butyl sulfonamide of Formula XVII is treatedwith two equivalents of n-butyl lithium at -50° to -80° intetrahydrofuran solution to give the dilithio salt XVIII.

Reaction (10b)

The salt XVIII is then immediately treated with one equivalent of achloro- or bromoaldehyde of Formula XXI at -70° to -80°. The temperatureis raised to 25° for 1 to 3 days, and the reaction is then quenched bythe addition of an acid such as acetic acid. The pure product, XIX, isisolated by stripping off the solvent and chromatographing orrecrystallizing the crude product.

Reaction (10c)

In this step the tert-butyl group is removed from XIX by heating thesecompounds in trifluoroacetic acid at 72° for 1-6 hours. The sulfonamidesof Formula IIg are isolated in pure form by stripping off thetrifluoroacetic acid solvent.

Sulfonamides of Formula IIj, which contain a dihydrofuran or adihydropyran group, can be prepared by the method shown in Equation 11.##STR38## wherein A" is ##STR39## X" is Cl or Br; and R₁, R₁₂, R₁₂ ',R₁₈, R₁₉, R₂₀, R₂₁, and R₂₂ are as previously defined.

Reaction (11a)

In this reaction a sulfonamide of Formula IIh is treated with oneequivalent of N-chlorosuccinimide or N-bromosuccinimide at 0°-60° in asolvent such as carbon tetrachloride or chloroform for 2-24 hours. Theby-product succinimide is removed by filtration and the solution carrieddirectly on to the next step.

Reaction (11b)

The sulfonamides of Formula IIi are dehydrohalogenated in carbontetrachloride or chloroform solution by treatment with at least oneequivalent of an appropriate base such as triethylamine, DABCO,pyridine, sodium methoxide or anhydrous potassium carbonate at 0°-60°for 1-6 hours. The products are isolated by washing the organic solutionwith water, drying, and stripping off the solvent. The sulfonamides ofFormula IIj can be obtained in pure form by recrystallization from asolvent such as ethanol, 1-chlorobutane, or acetonitrile, or by columnchromatography.

Sulfonamides containing a pyrrole group can be prepared by the sequenceof reactions shown in Equation 12. ##STR40## wherein Q' is ##STR41## andR₁, R₁₂, R₁₂ ', R₁₈, and R₁₉ are as previously defined.

Reaction (12a)

The lithio compounds of Formula XXI are prepared from the bromocompounds of Formula XX by treatment with n-butyl lithium at -80° ineither hexane/ether or hexane/tetrahydrofuran solvent systems. Thedetails of this type of transmetallation are further described by M. E.K. Cartoon and G. W. H. Cheeseman in J. Organometallic Chemistry, 212,1-9 (1981).

Reaction (12b)

The lithio compounds, XXII, are immediately treated with at least oneequivalent of sulfur dioxide at 0° to -50°. After warming to 25°, thelithium sulfinates of Formula XXIII are filtered off, and can be carrieddirectly on to reaction (12c).

Reaction (12c)

In this step chloramine is prepared at 0° by the addition of aqueoussodium hypochlorite to a stirred mixture of 30% ammonium hydroxidesolution and diethyl ether. The lithium sulfinates of Formula XXIII areadded to this mixture at 0° and the resulting mixture stirred at roomtemperature for 2-24 hours. The product sulfonamides are isolated byextraction into a solvent such as ethyl acetate and evaporation of thesolvent. The sulfonamides of Formula IIk may be purified byrecrystallization from solvents such as ethanol, 1-chlorobutane, oracetonitrile, or by column chromatography.

The bromo compounds of Formula XX can be prepared by methods well knownin the art, such as those reviewed by A. R. Jones and G. P. Bean in TheChemistry of Pyrroles, Academic Press, New York, N.Y., 1977.

Sulfonamides of Formula II in which Q is Q-11 can be prepared by thesequence of reactions shown in Equation 13.

Reaction (13a)

The dilithio salt of Formula XVIII is prepared as described above inreaction (10a) then treated with a ketone of Formula XXIV at -70° to-80°. The temperature is raised to 25° for 1 to 3 days, and the reactionis then quenched by the addition of an acid such as acetic acid. Theproduct, XXV, is isolated by evaporation of the solvent followed bychromatography or recrystallization. ##STR42## wherein R₁, R₁₂, R₁₂ ',R₁₈, R₁₉, R₂₀, R₂₁, R₂₂, R₂₃ and W' are as previously defined and atleast one of R₁₂, R₁₂ ', R₁₈ or R₁₉ is hydrogen.

Reaction (13b):

Removal of the tert-butyl group is accomplished by heating the aboveproducts, XXV, in trifluoroacetic acid at 72° for 1-6 hours. Dehydrationof the tertiary hydroxyl group occurs simultaneously and the isomericmixture of olefinic sulfonamides, XXVI, are isolated upon evaporation ofthe trifluoroacetic acid solvent.

In reaction (13c), sulfonamides of Formula XXVII are produced uponhydrogenation of the olefins, XXVI, under standard conditions.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by treating compounds of Formula I witha solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g., hydroxide, alkoxide, carbonate orhydride). Quaternary amine salts can be made by similar techniques.Detailed examples of such techniques are given in U.S. Pat. No.4,127,405, the disclosure of which is herein incorporated by reference.

The compounds of this invention and their preparation are furtherillustrated by the following examples wherein temperatures are given indegrees centrigrade and all parts are by weight unless otherwiseindicated.

EXAMPLE 1 Methyl 5-[(2-aminosulfonyl)phenyl]furan-2-carboxylate

To a solution of 65.1 g of methyl 5-(2-aminophenyl)furan-2-carboxylatein a mixture of 270 ml of concentrated hydrochloric acid and 75 ml ofglacial acetic acid was added a solution of 25.8 g of sodium nitrite in75 ml of water at -5° to 0° dropwise over a 30-minute period. Theresulting solution was stirred an additional 10 minutes at 0° beforebeing slowly added to a mixture of 6.0 g of cuprous chloride and 50 mlof sulfur dioxide in 375 ml of glacial acetic acid at ˜5°. This reactionmass was stirred at 0° for 1 hour and at 25° C. for 2 hours before beingpoured into 2.2 l of ice water. The intermediate sulfonyl chlorideprecipitated as an oil and was extracted into 1-chlorobutane, washedwith water, 5% sodium bicarbonate solution, and dried over anhydrousmagnesium sulfate.

The solution of the sulfonyl chloride in 1-chlorobutane was cooled to 5°and treated with 13.5 ml of anhydrous ammonia at 5°-10°. After stirringfor 30 minutes at 25°, the reaction mass was filtered and the solidwashed well with water and then 1-chlorobutane. The solid was dried invacuo at 60° to give 20.9 g of the title compound, mp=186.5°-188.5°.

NMR (DMSO-d₆) δ: 3.8 (s, 2.7H, CO₂ CH₃); 7.1-8.3 (m, 8.3H, 6aromatics+SO₂ NH₂).

EXAMPLE 22-(2-Carbomethoxyfur-5-yl)-N-(butylaminocarbonyl)benzenesulfonamide

A mixture of 16.9 g of the product of Example 1, 7.5 g of n-butylisocyanate, and 10.4 g of anhydrous potassium carbonate in 150 ml of2-butanone was stirred at 80° for 3 hours. The reaction mixture wascooled to 25°, poured into 550 ml of ice water and acidified to pH=1with concentrated hydrochloric acid. The precipitated solid wasfiltered, washed with water, and dried at 60° in vacuo to give 22.5 g ofthe title compound, mp=145°-148°.

NMR (DMSO-d₆) δ: 0.7-1.5 (m, 7.5H, 7 butyl's); 2.8-3.1 (m, 3.0H, 2butyl's); 3.9 (s, 2.8H, CO₂ CH₃); 6.2-6.5 (t, 0.9H, NH); 7.0-7.5 (m,1.9H, 2 furan's); 7.6-8.5 (m, 4.2H, 4 aromatics); ˜10.3 (broad singlet,0.7H, NH).

EXAMPLE 3 2-(2-Carbomethoxyfur-5-yl)benzenesulfonyl isocyanate

A solution of 19.0 g of the product of Example 2 and 0.1 g of1,4-diazabicyclo[2.2.2.]octane (DABCO) in 90 ml of dry xylenes washeated to reflux temperature (139° ). To this solution was added 3.6 mlof liquid phosgene over a period of about 2 hours, keeping thetemperature between 125° and 136° by adjusting the rate of phosgeneaddition. The reaction mixture was cooled to 25°, and filtered undernitrogen to remove DABCO hydrochloride. The filtrate was concentrated invacuo to give the title compound as a viscous, moisture-sensitive oil.This material was carried on to the desired products without furtherpurification.

IR (neat)=2280 cm⁻¹ (SO₂ NCO); 1760 cm⁻¹ (--CO₂ CH₃).

EXAMPLE 42-(2-Carbomethoxyfur-5-yl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

Under a nitrogen atmosphere, a mixture of 2.5 g of the product ofExample 3, 0.9 g of 2-amino-4,6-dimethoxypyrimidine, and a few crystalsof DABCO in 15 ml of dry acetonitrile was heated at 50°-55° for 1 hour,then stirred at 25° overnight. The solid was filtered off, washed withacetonitrile and 1-chlorobutane, and dried at 60° in vacuo to give 2.5 gof the title compound, mp=215°-217° (d).

NMR (DMSO-d₆) δ: 3.6, 3.8 (two singlets, 8.4H, 3CH₃ O's); 5.9 (s, 1.2H,Het-H); 6.9-8.4 (m, 6.2H, 6 aromatics); 10.7 (s, 1.0H, NH); 12-13(broad, 1.1H, NH).

Anal. Calcd. for C₁₉ H₁₈ N₄ O₈ S: C, 49.4; H, 3.9; N, 12.1. Found: C,49.6; H, 4.0; N, 12.4; C, 49.8; H, 4.1; N, 12.7.

Using the procedures described in the Equations and Examples above, thecompounds described in Tables 1-15 can be prepared.

                                      TABLE 1                                     __________________________________________________________________________     ##STR43##                                                                    R.sub.1                                                                            W R.sub.3                                                                           R.sub.5                                                                           R.sub.13                                                                         R.sub.17                                                                            W'                                                                              Z  X   Y          m.p. (°C.)                 __________________________________________________________________________    H    O H   H   H  CO.sub.2 CH.sub.3                                                                   O CH CH.sub.3 O                                                                        CH.sub.3 O 214-217 (d)                       H    O H   H   H  CO.sub.2 CH.sub.3                                                                   O N  CH.sub.3 O                                                                        CH.sub.3 O 210-212 (d)                       H    O H   H   H  CO.sub.2 CH.sub.3                                                                   O CH CH.sub.3 O                                                                        CH.sub.3   200-202 (d)                       H    O H   H   H  CO.sub.2 CH.sub.3                                                                   O N  CH.sub.3 O                                                                        CH.sub.3   198-199 (d)                       H    O H   H   H  CO.sub.2 CH.sub.3                                                                   O CH CH.sub.3                                                                          CH.sub.3   197-199 (d)                       H    O H   H   H  CO.sub.2 CH.sub.3                                                                   O N  CH.sub.3                                                                          CH.sub.3   205-207 (d)                       H    O H   H   H  H     O CH CH.sub.3 O                                                                        CH.sub.3 O 168-183 (d)                       H    O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3 O 175 (d)                           H    O H   H   H  H     O CH CH.sub.3 O                                                                        CH.sub.3   162-168 (d)                       H    S H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    S H   H   H  H     O CH CH.sub.3                                                                          CH.sub.3                                     H    O H   H   H  H     O N  CH.sub.3                                                                          CH.sub.3                                     H    O H   H   CH.sub.3                                                                         H     O N  CH.sub.3 O                                                                        CH.sub.3 O                                   H    O H   H   H  H     S CH CH.sub.3 O                                                                        CH.sub.3 O 193-196° d                 H    O H   H   H  H     S CH CH.sub.3 O                                                                        CH.sub.3   218- 219° d                H    O H   H   H  H     S CH CH.sub.3                                                                          CH.sub.3   211-215° d                 H    O H   H   H  H     S N  CH.sub.3 O                                                                        CH.sub.3 O >260°                      H    O H   H   H  H     S N  CH.sub.3 O                                                                        CH.sub.3   190-196° d                 H    O H   H   H  H     S N  CH.sub.3                                                                          CH.sub.3                                     H    O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3   165-186 (d)                       5-F  O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     5-Cl O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     5-Br O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     5-CF.sub.3                                                                         O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   H   H  H     O CH CH.sub.3                                                                          CH.sub.3   162-178 (d)                       5-CH.sub.3                                                                         O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     5-CH.sub.3 O                                                                       O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     3-Cl O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     4-Cl O H   H   H  H     O N  CH.sub. 3 O                                                                       CH.sub.3                                     6-Cl O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O CH.sub.3                                                                          H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O C.sub.2 H.sub.5                                                                   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O Cl  H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O Br  H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O CH.sub.3 O                                                                        H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O C.sub.2 H.sub.5 O                                                                 H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   CH.sub.3                                                                          H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   Cl  H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   CH.sub.3 O                                                                        H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O CH.sub.3                                                                          CH.sub.3                                                                          H  CH.sub.3                                                                            O N  CH.sub.3 O                                                                        CH.sub.3                                     H    S H   H   H  CH.sub.3                                                                            O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   H   H  C.sub.2 H.sub.5                                                                     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   H   H  Cl    O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   H   H  Br    O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   H   H  CH.sub.3 O                                                                          O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   H   H  C.sub.2 H.sub.5 O                                                                   O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   H   H  H     O N  CH.sub.3 O                                                                        CH.sub.3                                     H    O H   H   H  H     O CH Cl  CH.sub.3 O                                   H    O H   H   H  H     O CH Cl  NH.sub.2                                     H    O H   H   H  H     O CH CH.sub.3                                                                          CH.sub.2 OCH.sub.3                           H    O H   H   H  H     O CH CH.sub.3                                                                          C.sub.2 H.sub.5 O                            H    O H   H   H  H     O CH CH.sub.3                                                                          CH(OCH.sub.3).sub.2                          H    O H   H   H  H     O CH CH.sub.3 O                                                                        C.sub.2 H.sub.5                              H    O H   H   H  H     O N  CH.sub.3 O                                                                        NH.sub.2                                     H    O H   H   H  H     O N  CH.sub.3 O                                                                        NHCH.sub.3                                   H    O H   H   H  H     O N  CH.sub.3 O                                                                        N(CH.sub.3).sub.2                            H    O H   H   H  H     O CH CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                     H    O H   H   H  H     O CH CH.sub.3                                                                          OCH.sub.2 CF.sub.3                           H    O H   H   H  H     O CH OCH.sub.3                                                                         CF.sub.3                                     H    O H   H   H  H     O CH CH.sub.3                                                                          OCH.sub.2 CH.sub.2 OCH.sub.3                 H    O H   H   H  H     O N  CH.sub.3                                                                          SCH.sub.3                                    __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________     ##STR44##                                                                    R.sub.1                                                                            W  R.sub.3                                                                           R.sub.5                                                                           R.sub.13                                                                          R.sub.17                                                                            W' Z   X    Y          m.p. (°C.)            __________________________________________________________________________    H    O  H   H   H   H     O  CH  CH.sub.3 O                                                                         CH.sub.3 O                              H    O  H   H   H   H     O  CH  CH.sub.3 O                                                                         CH.sub.3                                H    O  H   H   H   H     O  CH  CH.sub.3                                                                           CH.sub.3                                H    O  H   H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3 O                              H    O  H   H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3                                H    O  H   H   H   H     O  N   CH.sub.3                                                                           CH.sub.3                                H    O  H   H   H   H     S  N   CH.sub.3 O                                                                         CH.sub.3                                H    O  H   H   H   H     S  N   CH.sub.3 O                                                                         CH.sub.3 O                              H    O  H   H   H   H     S  CH  CH.sub.3 O                                                                         CH.sub.3 O                              H    S  H   H   H   H     S  CH  CH.sub.3 O                                                                         CH.sub.3                                H    O  H   H   H   H     S  CH  CH.sub.3                                                                           CH.sub.3                                H    O  H   H   CH.sub.3                                                                          H     O  N   CH.sub.3 O                                                                         CH.sub.3 O                              5-Cl O  H   H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3 O                              5-Br O  H   H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3                                5-CH.sub.3                                                                         O  H   H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3                                6-Cl O  H   H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3                                6-CH.sub.3                                                                         O  H   H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3                                H    O  CH.sub.3                                                                          H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3                                H    O  C.sub.2 H.sub.5                                                                   H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3                                H    O  CH.sub.3                                                                          CH.sub.3                                                                          H   CH.sub.3                                                                            O  N   CH.sub.3 O                                                                         CH.sub.3                                H    O  H   CH.sub.3                                                                          H   H     O  N   CH.sub.3 O                                                                         CH.sub.3                                H    S  H   H   H   C.sub.2 H.sub.5                                                                     O  N   CH.sub.3 O                                                                         CH.sub.3                                H    O  H   H   H   CO.sub.2 CH.sub.3                                                                   O  N   CH.sub.3 O                                                                         CH.sub.3                                H    O  H   H   H   H     O  N   CH.sub.3 O                                                                         CH.sub.3 O                              H    O  H   H   H   H     O  CH  CH.sub.3 O                                                                         CH.sub.3 O                              H    O  H   H   H   H     O  CH  CH.sub.3 O                                                                         CH.sub.3                                H    O  H   H   H   H     O  CH  Cl   CH.sub.3 O                              H    O  H   H   H   H     O  CH  CH.sub.3                                                                           CH.sub.2 OCH.sub.3                      H    S  H   H   H   H     O  CH  CH.sub.3                                                                           CH(OCH.sub.3).sub.2                     H    O  H   H   H   H     O  N   CH.sub.3 O                                                                         NH.sub.2                                H    O  H   H   H   H     O  N   CH.sub.3 O                                                                         NHCH.sub.3                              H    O  H   H   H   H     O  N   CH.sub. 3 O                                                                        N(CH.sub.3).sub.2                       H    O  H   H   H   H     O  CH  CH.sub.3                                                                           OCH.sub.2 CF.sub.3                      H    O  H   H   H   H     O  CH  OCH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________     ##STR45##                                                                    R.sub.1                                                                             W  R.sub.12                                                                          R' .sub.12                                                                        R.sub.13                                                                          R.sub.18                                                                          R.sub.19                                                                          Z   X    Y       m.p. (°C.)               __________________________________________________________________________    H     O  H   H   H   H   H   CH  CH.sub.3 O                                                                         CH.sub.3 O                              H     O  H   H   H   H   H   CH  CH.sub.3 O                                                                         CH.sub.3                                H     O  H   H   H   H   H   CH  CH.sub.3                                                                           CH.sub.3                                H     S  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3 O                              H     O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                H     O  H   H   H   H   H   N   CH.sub.3                                                                           CH.sub.3                                H     O  CH.sub.3                                                                          H   H   H   CH.sub.3                                                                          CH  CH.sub.3 O                                                                         CH.sub.3 O                              H     O  CH.sub.3                                                                          H   H   H   CH.sub.3                                                                          CH  CH.sub.3 O                                                                         CH.sub.3                                H     O  CH.sub.3                                                                          H   H   H   CH.sub.3                                                                          CH  CH.sub.3                                                                           CH.sub.3                                H     O  CH.sub.3                                                                          H   H   H   CH.sub.3                                                                          N   CH.sub.3 O                                                                         CH.sub.3 O                              H     O  CH.sub.3                                                                          H   H   H   CH.sub.3                                                                          N   CH.sub.3 O                                                                         CH.sub.3                                H     O  H   H   CH.sub.3                                                                          H   H   N   CH.sub.3 O                                                                         CH.sub.3 O                              5-Cl  O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3 O                              5-F   O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                5-Br  O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                5-CH.sub.3                                                                          O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                5-CF.sub.3                                                                          O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                5-OCH.sub.3                                                                         O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                3-Cl  O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                4-Cl  O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                6-Cl  O  H   H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                H     O  CH.sub.3                                                                          CH.sub.3                                                                          H   CH.sub.3                                                                          CH.sub.3                                                                          N   CH.sub.3 O                                                                         CH.sub.3                                H     O  CH.sub.3                                                                          H   H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                H     O  H   CH.sub.3                                                                          H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                H     O  H   CH.sub.3                                                                          H   CH.sub.3                                                                          H   N   CH.sub.3 O                                                                         CH.sub.3                                H     O  CH.sub.3                                                                          CH.sub.3                                                                          H   H   H   N   CH.sub.3 O                                                                         CH.sub.3                                H     O  H   H   H   H   H   CH  CH.sub.3                                                                           C.sub.2 H.sub.5 O                       H     S  H   H   H   H   H   CH  CH.sub.3                                                                           CH.sub.2 OCH.sub.3                      H     O  H   H   H   H   H   CH  CH.sub.3                                                                           CH(OCH.sub.3).sub.2                     H     O  H   H   H   H   H   CH  Cl   CH.sub.3 O                              H     O  H   H   H   H   H   N   CH.sub.3 O                                                                         N(CH.sub.3).sub. 2                      H     O  H   H   H   H   H   N   CH.sub.3 O                                                                         NH.sub.2                                __________________________________________________________________________

                  TABLE 4                                                         ______________________________________                                         ##STR46##                                                                                                            m.p.                                  R.sub.1                                                                              W R.sub.12                                                                            R' .sub.12                                                                           R.sub.13 R.sub.18                                                                    Z    X     Y (°C.)                        ______________________________________                                        H      O H     H      H   H    CH   CH.sub.3 O                                                                          CH.sub.3 O                          H      OH      H      H   H    CH   CH.sub.3 O                                                                          CH.sub.3                            H      OH      H      H   H    CH   CH.sub.3                                                                            CH.sub.3                            H      OH      H      H   H    N    CH.sub.3 O                                                                          CH.sub.3 O                          H      OH      H      H   H    N    CH.sub.3 O                                                                          CH.sub.3                            H      OH      H      H   CH.sub.3                                                                           CH   CH.sub.3 O                                                                          CH.sub.3 O                          H      OH      H      H   CH.sub.3                                                                           CH   CH.sub.3 O                                                                          CH.sub.3                            H      SH      H      H   CH.sub.3                                                                           N    CH.sub.3 O                                                                          CH.sub.3 O                          H      OH      H      H   CH.sub.3                                                                           N    CH.sub.3 O                                                                          CH.sub.3                            H      OCH.sub.3                                                                             CH.sub.3                                                                             H   CH.sub.3                                                                           N    CH.sub.3 O                                                                          CH.sub.3                            H      OCH.sub.3                                                                             CH.sub.3                                                                             H   H    N    CH.sub.3 O                                                                          CH.sub.3                            H      SCH.sub.3                                                                             H      H   H    N    CH.sub.3 O                                                                          CH.sub.3                            H      OH      CH.sub.3                                                                             H   H    N    CH.sub.3 O                                                                          CH.sub.3                            H      OH      H      CH.sub.3                                                                           H   N    CH.sub.3 O                                                                          CH.sub.3 O                          5-F    OH      H      H    H   N    CH.sub.3 O                                                                          CH.sub.3 O                          5-Br   OH      H      H    H   N    CH.sub.3 O                                                                          CH.sub.3 O                          5-CH.sub.3                                                                           OH      H      H    H   N    CH.sub.3 O                                                                          CH.sub.3 O                          5-CH.sub.3 O                                                                         OH      H      H    H   N    CH.sub.3 O                                                                          CH.sub.3 O                          5-CF.sub.3                                                                           OH      H      H    H   N    CH.sub.3 O                                                                          CH.sub.3 O                          5-Cl   OH      H      H    H   N    CH.sub.3 O                                                                          CH.sub.3 O                          H      OH      H      H    H   CH   Cl    CH.sub.3 O                          H      OH      H      H    H   CH   CH.sub.3                                                                            CH.sub.2 OCH.sub.3                  H      OH      H      H    H   CH   CH.sub.3                                                                            CH(OCH.sub.3).sub.2                 H      OH      H      H    H   N    CH.sub.3                                                                            C.sub.2 H.sub.5 O                   H      OH      H      H    H   N    CH.sub.3 O                                                                          N(CH.sub.3).sub.2                   H      OH      H      H    H   CH   Cl    NH.sub.2                            ______________________________________                                    

                                      TABLE 5                                     __________________________________________________________________________     ##STR47##                                                                    R.sub.1                                                                            W R.sub.12                                                                         R.sub.12 '                                                                       R.sub.13                                                                         R.sub.18                                                                         Z  X   Y          m.p.(°C.)                         __________________________________________________________________________    H    O H  H  H  H  CH CH.sub.3 O                                                                        CH.sub.3 O                                          H    O H  H  H  H  CH CH.sub.3 O                                                                        CH.sub.3                                            H    O H  H  H  H  CH CH.sub.3                                                                          CH.sub.3                                            H    O H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3 O                                          H    O H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                            H    O CH.sub.3                                                                         H  H  CH.sub.3                                                                         CH CH.sub.3 O                                                                        CH.sub.3 O                                          H    O CH.sub.3                                                                         H  H  CH.sub.3                                                                         CH CH.sub.3 O                                                                        CH.sub.3                                            H    S CH.sub.3                                                                         H  H  CH.sub.3                                                                         N  CH.sub.3 O                                                                        CH.sub.3 O                                          H    S CH.sub.3                                                                         H  H  CH.sub.3                                                                         N  CH.sub.3 O                                                                        CH.sub.3                                            H    O CH.sub.3                                                                         CH.sub.3                                                                         H  CH.sub.3                                                                         N  CH.sub.3 O                                                                        CH.sub.3                                            H    O H  H  CH.sub.3                                                                         H  N  CH.sub.3 O                                                                        CH.sub.3 O                                          H    O H  CH.sub.3                                                                         H  H  N  CH.sub.3 O                                                                        CH.sub.3                                            H    O H  H  H  CH.sub.3                                                                         N  CH.sub.3 O                                                                        CH.sub.3                                            5-F  O H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                            3-Br O H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                            4-CH.sub.3                                                                         O H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                            6-Cl O H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                            5-CF.sub.3                                                                         O H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                            5-CH.sub.3 O                                                                       O H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                            H    O H  H  H  H  CH Cl  CH.sub.3 O                                          H    O H  H  H  H  CH CH.sub.3                                                                          CH(OCH.sub.3).sub.2                                 H    O H  H  H  H  CH CH.sub.3 O                                                                        CH.sub.2 OCH.sub.3                                  H    O H  H  H  H  N  CH.sub.3 O                                                                        N(CH.sub.3).sub.2                                   H    O H  H  H  H  N  CH.sub.3                                                                          NHCH.sub.3                                          H    O H  H  H  H  N  CH.sub.3 O                                                                        NH.sub.2                                            H    S H  H  H  H  CH CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                            H    O H  H  H  H  CH OCH.sub.3                                                                         CF.sub.3                                            __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________     ##STR48##                                                                                                                  m.p.                            R.sub.1                                                                            W R.sub.13                                                                         R.sub.12                                                                         R.sub.12 '                                                                       R.sub.18                                                                         R.sub.19                                                                         R.sub.20                                                                         R.sub.21                                                                         W'                                                                              Z  X   Y        (°C.)                    __________________________________________________________________________    H    O H  H  H  H  H  H  H  O CH CH.sub. 3 O                                                                       CH.sub.3 O                               H    O H  H  H  H  H  H  H  O CH CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  O CH CH.sub.3                                                                          CH.sub.3                                 H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3 O                               H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  O N  CH.sub.3                                                                          CH.sub.3                                 H    O H  H  H  H  H  H  H  S CH CH.sub.3 O                                                                        CH.sub.3 O                               H    O H  H  H  H  H  H  H  S CH CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  S CH CH.sub.3                                                                          CH.sub.3                                 H    O H  H  H  H  H  H  H  S N  CH.sub.3 O                                                                        CH.sub.3 O                               H    S H  H  H  H  H  H  H  S N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  S N  CH.sub.3                                                                          CH.sub.3                                 H    O CH.sub.3                                                                         H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3 O                               H    O H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                         O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  CH.sub.3                                                                         H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  CH.sub.3                                                                         H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  CH.sub.3                                                                         H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         CH.sub.3                                                                         O N  CH.sub.3 O                                                                        CH.sub.3                                 5-F  O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 3-Br O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 4-CH.sub.3                                                                         O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 6-Cl O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 5-CF.sub.3                                                                         O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 5-CH.sub.3                                                                         O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 5-CH.sub.3 O                                                                       O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 5-Cl O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  O CH Cl  CH.sub.3 O                               H    O H  H  H  H  H  H  H  O CH CH.sub.3                                                                          CH(OCH.sub.3).sub.2                      H    S H  H  H  H  H  H  H  O CH CH.sub.3 O                                                                        CH.sub.2 OCH.sub.3                       H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        N(CH.sub.3).sub.2                        H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        NHCH.sub.3                               H    O H  H  H  H  H  H  H  O N  CH.sub.3                                                                          NH.sub.2                                 H    O H  H  H  H  H  H  H  O N  CH.sub.3                                                                          C.sub.2 H.sub.5 O                        H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        C.sub.2 H.sub.5                          H    O H  H  H  H  H  H  H  O CH CH.sub.3                                                                          OCH.sub.2 CH.sub.2 OCH.sub.3             __________________________________________________________________________

                                      TABLE 7                                     __________________________________________________________________________     ##STR49##                                                                    R.sub.1                                                                            W R.sub.13                                                                         R.sub.12                                                                         R.sub.12 '                                                                       R.sub.18                                                                         R.sub.19                                                                         R.sub.20                                                                         R.sub.21                                                                         W'                                                                              Z  X   Y      m.p.(°C.)                  __________________________________________________________________________    H    O H  H  H  H  H  H  H  O CH CH.sub.3 O                                                                        CH.sub.3 O                                                                           183-185°                   H    O H  H  H  H  H  H  H  O CH CH.sub.3 O                                                                        CH.sub.3                                                                             185-186°                   H    S H  H  H  H  H  H  H  O CH CH.sub.3                                                                          CH.sub.3                                 H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3 O                                                                           171-180°                   H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                                                             181-186° (d)               H    O H  H  H  H  H  H  H  O N  CH.sub.3                                                                          CH.sub.3                                 H    O CH.sub.3                                                                         H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  S CH CH.sub.3 O                                                                        CH.sub.3 O                               H    O H  H  H  H  H  H  H  S CH CH.sub.3 O                                                                        CH.sub.3                                 H    S H  H  H  H  H  H  H  S CH CH.sub.3                                                                          CH.sub.3                                 H    O H  H  H  H  H  H  H  S N  CH.sub.3 O                                                                        CH.sub.3 O                               H    O H  H  H  H  H  H  H  S N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  S N  CH.sub.3                                                                          CH.sub.3                                 H    O H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                         O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  CH.sub.3                                                                         CH.sub.3                                                                         O N  CH.sub.3 O                                                                        CH.sub.3                                 5-F  O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 5-Br O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 5-CH.sub.3                                                                         O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 5-CF.sub.3                                                                         O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 5-Cl O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  O CH CH.sub.3                                                                          CH.sub.3                                                                             184-187°                   5-CH.sub.3 O                                                                       O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 3-Cl O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 4-Cl O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 6-Cl O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  O CH Cl  CH.sub.3 O                               H    O H  H  H  H  H  H  H  O CH CH.sub.3 O                                                                        CH.sub.2 OCH.sub.3                       H    O H  H  H  H  H  H  H  O CH CH.sub.3 O                                                                        CH(OCH.sub.3).sub.2                      H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        N(CH.sub.3).sub.2                        H    O H  H  H  H  H  H  H  O N  CH.sub.3                                                                          NHCH.sub.3                               H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        NH.sub.2                                 H    O H  H  H  H  H  H  H  O N  CH.sub.3                                                                          C.sub.2 H.sub.5 O                        H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        C.sub.2 H.sub.5                          H    O H  H  H  H  H  H  H  O N  CH.sub.3                                                                          OCH.sub.2 CF.sub.3                       __________________________________________________________________________

                                      TABLE 8                                     __________________________________________________________________________     ##STR50##                                                                    R.sub.1                                                                            W R.sub.13                                                                         R.sub.12                                                                         R.sub.12 '                                                                       R.sub.18                                                                         R.sub.19                                                                         R.sub.20                                                                         R.sub.21                                                                         W'                                                                              Z  X   Y      m.p.(°C.)                  __________________________________________________________________________    H    O H  H  H  H  H  H       CH CH.sub.3 O                                                                        CH.sub.3 O                               H    O H  H  H  H  H  H       CH CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H       CH CH.sub.3                                                                          CH.sub.3                                 H    O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3 O                               H    O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H       N  CH.sub.3                                                                          CH.sub.3                                 H    O CH.sub.3                                                                         H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 H    S H  CH.sub.3                                                                         H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                              N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  CH.sub.3                                                                         H  CH.sub.3                                                                         CH.sub.3                                                                         H       N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                              N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  CH.sub.3                                                                              N  CH.sub.3 O                                                                        CH.sub.3                                 5-F  O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 5-Cl O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 5-CH.sub.3                                                                         O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 5-Br O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 5-CF.sub.3                                                                         O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 5-CH.sub.3 O                                                                       O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 3-Cl O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 4-Cl O H  H  H  H  H  H       N  CH.sub.3 O                                                                        CH.sub.3                                 6-Cl O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        CH.sub.3                                 H    O H  H  H  H  H  H  H  O CH Cl  CH.sub.3 O                               H    O H  H  H  H  H  H  H  O CH Cl  NH.sub.2                                 H    O H  H  H  H  H  H  H  O CH CH.sub. 3                                                                         CH.sub.2 OCH.sub.3                       H    O H  H  H  H  H  H  H  O CH CH.sub.3 O                                                                        CH(OCH.sub.3).sub.2                      H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        N(CH.sub.3).sub.2                        H    O H  H  H  H  H  H  H  O N  CH.sub.3                                                                          NH.sub.2                                 H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        C.sub.2 H.sub.5 O                        H    S H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        C.sub.2 H.sub.5                          H    O H  H  H  H  H  H  H  O N  CH.sub.3 O                                                                        NH(CH.sub.3).sub.2                       __________________________________________________________________________

                                      TABLE 9                                     __________________________________________________________________________     ##STR51##                                                                                                                 m.p.                             R.sub.1                                                                            W R.sub.13                                                                         R.sub.12                                                                         R.sub.12 '                                                                       R.sub.18                                                                         R.sub.19                                                                         R.sub.20                                                                         R.sub.21                                                                         R.sub.22                                                                         Z  X   Y      (°C.)                     __________________________________________________________________________    H    O H  H  H  H  H  H  H  H  CH CH.sub.3 O                                                                        CH.sub.3 O                              H    S H  H  H  H  H  H  H  H  CH CH.sub.3 O                                                                        CH.sub.3                                H    O H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          CH.sub.3                                H    O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3 O                              H    O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                H    O H  H  H  H  H  H  H  H  N  CH.sub.3                                                                          CH.sub.3                                H    O CH.sub.3                                                                         H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3 O                              H    O H  CH.sub.3                                                                         H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                H    O H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                H    O H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                         H  H  N  CH.sub.3 O                                                                        CH.sub.3                                H    O H  H  H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                         N  CH.sub.3 O                                                                        CH.sub.3                                H    O H  CH.sub.3                                                                         H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                         N  CH.sub.3 O                                                                        CH.sub.3                                H    S H  CH.sub.3                                                                         CH.sub.3                                                                         H  CH.sub.3                                                                         H  CH.sub.3                                                                         H  N  CH.sub.3 O                                                                        CH.sub.3                                5-Cl O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                5-F  O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                5-CH.sub.3                                                                         O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                5-Br O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                5-CF.sub.3                                                                         O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                5-CH.sub.3 O                                                                       O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                3-Cl O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                4-Cl O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                6-Cl O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        CH.sub.3                                H    O H  H  H  H  H  H  H  H  CH Cl  CH.sub.3 O                              H    O H  H  H  H  H  H  H  H  CH Cl  NH.sub.2                                H    O H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          CH.sub.2 OCH.sub.3                      H    O H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          CH(OCH.sub.3).sub.2                     H    O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        N(CH.sub.3).sub.2                       H    O H  H  H  H  H  H  H  H  N  CH.sub.3                                                                          NH.sub.2                                H    O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        NHCH.sub.3                              H    O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        C.sub.2 H.sub.5 O                       H    O H  H  H  H  H  H  H  H  N  CH.sub.3 O                                                                        C.sub.2 H.sub.5                         H    O H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          SCH.sub.3                               __________________________________________________________________________

                                      TABLE 10                                    __________________________________________________________________________     ##STR52##                                                                                                                         m.p.                     R.sub.1                                                                           W W'                                                                              R.sub.12                                                                         R.sub.12 '                                                                       R.sub.13                                                                         R.sub.18                                                                         R.sub.19                                                                         R.sub.20                                                                         R.sub.21                                                                         R.sub.22                                                                         R.sub.23                                                                         Z  X   Y          (°C.)             __________________________________________________________________________    H   O O H  H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          CH.sub.3                            H   O O H  H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          OCH.sub.3                           H   O O H  H  H  H  H  H  H  H  H  CH OCH.sub.3                                                                         OCH.sub.3                           H   O O H  H  H  H  H  H  H  H  H  N  CH.sub.3                                                                          OCH.sub.3                           H   S O H  H  H  H  H  H  H  H  H  N  OCH.sub.3                                                                         OCH.sub.3                           H   O O H  H  H  H  H  H  H  H  H  N  OCH.sub.3                                                                         OCH.sub.3                           H   O S H  H  CH.sub.3                                                                         H  H  H  H  H  H  N  CH.sub.3                                                                          OCH.sub.3                           H   S S H  H  H  H  H  H  H  H  H  CH Cl  OCH.sub.3                           H   O S H  H  H  H  H  H  H  H  H  CH OCH.sub.3                                                                         CF.sub.3                            H   O S H  H  H  H  CH.sub.3                                                                         H  H  H  H  CH CH.sub.3                                                                          SCH.sub.3                           H   O O CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H  H  H  N  CH.sub.3                                                                          OCH.sub.2 CF.sub.3                  H   O O CH.sub.3                                                                         H  H  CH.sub.3                                                                         H  H  H  H  H  N  OCH.sub.3                                                                         OC.sub.2 H.sub.5                    H   O O H  H  H  H  H  CH.sub.3                                                                         H  H  H  N  OCH.sub.3                                                                         CH.sub.3                            H   O O CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                         CH CH.sub.3                                                                          C.sub.2 H.sub.5                     H   O O H  H  H  H  H  H  CH.sub.3                                                                         H  H  CH OCH.sub.3                                                                         CH.sub.3                            H   O O H  H  H  H  H  H  H  CH.sub.3                                                                         H  CH CH.sub.3                                                                          CH.sub.3                            H   O O H  H  H  H  H  H  H  H  H  N  OCH.sub.3                                                                         OCH.sub.2 CH.sub.2 OCH.sub.3        H   O S H  H  H  H  H  H  H  H  H  N  CH.sub.3                                                                          OCH.sub.3                           H   O S H  H  H  H  H  H  H  H  H  N  CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)            5-Cl                                                                              O O H  H  H  H  H  H  H  H  H  CH OCH.sub.3                                                                         CH.sub.3                            5-CH.sub.3                                                                        O O H  H  H  H  H  H  H  H  H  CH Cl  OCH.sub. 3                          6-Cl                                                                              O O H  H  H  H  H  H  H  H  H  CH OCH.sub.3                                                                         CH.sub.2 OCH.sub.3                  4-CH.sub.3                                                                        O O H  H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          OCH.sub.3                           __________________________________________________________________________

                                      TABLE 11                                    __________________________________________________________________________     ##STR53##                                                                                                                         m.p.                     R.sub.1                                                                           W W'                                                                              R.sub.12                                                                         R.sub.12 '                                                                       R.sub.13                                                                         R.sub.18                                                                         R.sub.19                                                                         R.sub.20                                                                         R.sub.21                                                                         R.sub.22                                                                         R.sub.23                                                                         Z  X   Y          (°C.)             __________________________________________________________________________    H    O                                                                              O H  H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          CH.sub.3                            H   O O H  H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          OCH.sub.3                           H   O O H  H  H  H  H  H  H  H  H  CH OCH.sub.3                                                                         OCH.sub.3                           H   O O H  H  H  H  H  H  H  H  H  N  CH.sub.3                                                                          OCH.sub.3                           H   S O H  H  H  H  H  H  H  H  H  N  OCH.sub.3                                                                         OCH.sub.3                           H   O O H  H  H  H  H  H  H  H  H  N  OCH.sub.3                                                                         OCH.sub.3                           H   O S H  H  CH.sub.3                                                                         H  H  H  H  H  H  N  CH.sub.3                                                                          OCH.sub.3                           H   S S H  H  H  H  H  H  H  H  H  CH Cl  OCH.sub.3                           H   O S H  H  H  H  H  H  H  H  H  CH OCH.sub.3                                                                         CF.sub.3                            H   O S H  H  H  H  CH.sub.3                                                                         H  H  H  H  CH CH.sub.3                                                                          SCH.sub.3                           H   O O CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H  H  H  N  CH.sub.3                                                                          OCH.sub.2 CF.sub.3                  H   O O CH.sub.3                                                                         H  H  CH.sub.3                                                                         H  H  H  H  H  N  OCH.sub.3                                                                         OC.sub.2 H.sub.5                    H   O O H  H  H  H  H  CH.sub.3                                                                         H  H  H  N  OCH.sub.3                                                                         CH.sub.3                            H   O O CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H  CH.sub.3                                                                         CH.sub.3                                                                         CH CH.sub.3                                                                          C.sub.2 H.sub.5                     H   O O H  H  H  H  H  H  CH.sub.3                                                                         H  H  CH OCH.sub.3                                                                         CH.sub.3                            H   O O H  H  H  H  H  H  H  CH.sub.3                                                                         H  CH CH.sub.3                                                                          CH.sub.3                            H   O O H  H  H  H  H  H  H  H  H  N  OCH.sub.3                                                                         OCH.sub.2 CH.sub.2 OCH.sub.3        H   O S H  H  H  H  H  H  H  H  H  N  CH.sub.3                                                                          OCH.sub.3                           H   O S H  H  H  H  H  H  H  H  H  N  CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)            5-Cl                                                                              O O H  H  H  H  H  H  H  H  H  CH OCH.sub.3                                                                         CH.sub.3                            5-CH.sub.3                                                                        O O H  H  H  H  H  H  H  H  H  CH Cl  OCH.sub.3                           6-Cl                                                                              O O H  H  H  H  H  H  H  H  H  CH OCH.sub.3                                                                         CH.sub.2 OCH.sub.3                  4-CH.sub. 3                                                                       O O H  H  H  H  H  H  H  H  H  CH CH.sub.3                                                                          OCH.sub.3                           __________________________________________________________________________

                  TABLE 12                                                        ______________________________________                                         ##STR54##                                                                    Q             R.sub.1                                                                              R.sub.13                                                                             X.sub.1                                                                             G    m.p. (°C.)                      ______________________________________                                         ##STR55##    H      H      CH.sub.3                                                                            CH.sub.2                                     ##STR56##    H      H      CH.sub.3                                                                            O                                            ##STR57##    H      H      CH.sub.3                                                                            O                                            ##STR58##    H      H      CH.sub.3                                                                            O                                            ##STR59##    H      H      CH.sub.3                                                                            O                                            ##STR60##    H      H      OCH.sub.3                                                                           O                                            ##STR61##    H      H      OCH.sub.3                                                                           CH.sub.2                                     ##STR62##    5-Cl   H      CH.sub.3                                                                            O                                            ##STR63##    H      H      CH.sub.3                                                                            O                                            ##STR64##    H      CH.sub.3                                                                             CH.sub.3                                                                            O                                            ##STR65##    H      H      Cl    O                                            ##STR66##    H      H      CH.sub.3                                                                            O                                            ##STR67##    H      H      CH.sub.3                                                                            O                                            ##STR68##    H      H      CH.sub.3                                                                            CH.sub.2                                     ##STR69##    H      H      CH.sub.3                                                                            O                                            ##STR70##    H      H      CH.sub.3                                                                            O                                            ##STR71##    H      H      CH.sub.3                                                                            O                                            ##STR72##    H      H      CH.sub.3                                                                            O                                           ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                         ##STR73##                                                                    Q              R.sub.1                                                                              R.sub.13                                                                              X.sub.1                                                                             m.p. (°C.)                         ______________________________________                                         ##STR74##     H      H       CH.sub.3                                         ##STR75##     H      H       CH.sub.3                                         ##STR76##     H      H       CH.sub.3                                         ##STR77##     H      H       CH.sub.3                                         ##STR78##     H      H       CH.sub.3                                         ##STR79##     H      H       OCH.sub.3                                        ##STR80##     H      H       OCH.sub.3                                        ##STR81##     5-Cl   H       CH.sub.3                                         ##STR82##     H      H       CH.sub.3                                         ##STR83##     H      CH.sub.3                                                                              CH.sub.3                                         ##STR84##     H      H       Cl                                               ##STR85##     H      H       CH.sub.3                                         ##STR86##     H      H       CH.sub.3                                         ##STR87##     H      H       CH.sub.3                                         ##STR88##     H      H       CH.sub.3                                         ##STR89##     H      H       CH.sub.3                                         ##STR90##     H      H       CH.sub.3                                         ##STR91##     H      H       CH.sub.3                                        ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                         ##STR92##                                                                    Q              R.sub.1                                                                              R.sub.13                                                                              X.sub.1                                                                             m.p. (°C.)                         ______________________________________                                         ##STR93##     H      H       CH.sub.3                                         ##STR94##     H      H       CH.sub.3                                         ##STR95##     H      H       CH.sub.3                                         ##STR96##     H      H       CH.sub.3                                         ##STR97##     H      H       CH.sub.3                                         ##STR98##     H      H       OCH.sub. 3                                       ##STR99##     H      H       OCH.sub.3                                        ##STR100##    5-Cl   H       CH.sub.3                                         ##STR101##    H      H       CH.sub.3                                         ##STR102##    H      CH.sub.3                                                                              CH.sub.3                                         ##STR103##    H      H       Cl                                               ##STR104##    H      H       CH.sub.3                                         ##STR105##    H      H       CH.sub.3                                         ##STR106##    H      H       CH.sub.3                                         ##STR107##    H      H       CH.sub.3                                         ##STR108##    H      H       CH.sub.3                                         ##STR109##    H      H       CH.sub.3                                         ##STR110##    H      H       CH.sub.3                                        ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                         ##STR111##                                                                   Q            R.sub.1                                                                              X.sub.2    Y.sub.2                                                                             m.p. (°C.)                        ______________________________________                                         ##STR112##  H      CH.sub.3   OCH.sub.3                                       ##STR113##  H      C.sub.2 H.sub.5                                                                          OCH.sub.3                                       ##STR114##  H      CH.sub.3   SCH.sub.3                                       ##STR115##  H      C.sub.2 H.sub.5                                                                          SCH.sub.3                                       ##STR116##  H      CH.sub.2 CF.sub.3                                                                        SC.sub.2 H.sub.5                                ##STR117##  H      CH.sub.2 CF.sub.3                                                                        SC.sub. 2 H.sub.5                               ##STR118##  5-F    CH.sub.3   SCH.sub.3                                       ##STR119##  H      CH.sub.2 CH.sub.2 CH.sub.3                                                               OC.sub.2 H.sub.5                                ##STR120##  H      C.sub.2 H.sub.5                                                                          OCH.sub.3                                      ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

                  TABLE 16                                                        ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 5 Wettable Powder

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-diode: 80%

sodium alkylnaphthalenesulfonate: 2%

sodium ligninsulfonate: 2%

synthetic amorphous silica: 3%

kaolinite: 13%

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 6 Wettable Powder

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 50%

sodium alkylnaphthalenesulfonate: 2%

low viscosity methyl cellulose: 2%

diatomaceous earth: 46%

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 7 Granule

Wettable Powder of Example 6: 5%

attapulgite granules (U.S.S. 20-40 mesh; 0.84-0.42 mm): 95%

A slurry of wettable powder containing ≈25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 8 Extruded Pellet

N-[(4-methoxymethyl-6-methylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 25%

anhydrous sodium sulfate: 10%

crude calcium ligninsulfonate: 5%

sodium alkylnaphthalenesulfonate: 1%

calcium/magnesium bentonite: 59%

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 9 Oil Suspension

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 25%

polyoxyethylene sorbitol hexaoleate: 5%

highly aliphatic hydrocarbon oil: 70%

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 10 Wettable Powder

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 20%

sodium alkylnaphthalenesulfonate: 4%

sodium ligninsulfonate: 4%

low viscosity methyl cellulose: 3%

attapulgite: 69%

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 11 Low Strength Granule

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 1%

N,N-dimethylformamide: 9%

attapulgite granules (U.S.S. 20-40 sieve): 90%

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 12 Aqueous Suspension

N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-diode: 40%

polyacrylic acid thickener: 0.3%

dodecylphenol polyethylene glycol ether: 0.5%

disodium phosphate: 1%

monosodium phosphate: 0.5%

polyvinyl alcohol: 1.0%

water: 56.7%

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 13 Solution

N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide, sodium salt: 5%

water: 95%

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 14 Low Strength Granule

N-[(4-methoxymethyl-6-methylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 0.1%

attapulgite granules (U.S.S. 20-40 mesh): 99.9%

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 15 Granule

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 80%

wetting agent: 1%

crude ligninsulfonate salt (containing 5-20% of the natural sugars): 10%

attapulgite clay: 9%

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 16 High Strength Concentrate

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 99%

silica aerogel: 0.5%

synthetic amorphous silica: 0.5%

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 17 Wettable Powder

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 90%

dioctyl sodium sulfosuccinate: 0.1%

synthetic fine silica: 9.9%

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 18 Wettable Powder

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 40%

sodium ligninsulfonate: 20%

montmorillonite clay: 40%

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 19 Oil Suspension

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 35%

blend of polyalcohol carboxylic esters and oil soluble petroleumsulfonates: 6%

xylene: 59%

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The produce can beused directly, extended with oils, or emulsified in water.

EXAMPLE 20 Dust

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-1,2-benzisothiazole-7-sulfonamide,1,1-dioxide: 10%

attapulgite: 10%

Pyrophyllite: 80%

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

Utility

The compounds of the present invention are powerful herbicides. Theyhave utility for broadspectrum pre- and/or post-emergence weed controlin areas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,parking lots, drive-in theaters, around billboards, highway and railroadstructures. Alternatively, the subject compounds are useful for theselective pre- or post-emergence weed control in crops, such as wheat,barley and corn.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as selective orgeneral herbicides, the crop species involved, the types of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.01 to 5 kg/ha,the lower rates being suggested for use on lighter soils and/or thosehaving a low organic matter content, for selective weed control or forsituations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.##STR121##

Test A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia),morningglory (Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn,soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were plantedin a growth medium and treated pre-emergence with a nonphytotoxicsolvent solution of the compounds of Table A. At the same time, cottonhaving five leaves (including cotyledonary ones), bush beans with thethird trifoliolate leaf expanding, crabgrass with two leaves,barnyardgrass with two leaves, wild oats with two leaves, sicklepod withthree leaves (including cotyledonary ones), morningglory with fourleaves (including the cotyledonary ones) cocklebur with four leaves(including the cotyledonary ones), sorghum with four leaves, corn withfour leaves, soybean with two cotyledonary leaves, rice with threeleaves, wheat with one leaf, and nutsedge with three to five leaves weresprayed with a nonphytotoxic solvent solution of the compounds of TableA. Other containers of the above mentioned weeds and crops were treatedpre- or post-emergence with the same nonphytotoxic solvent so as toprovide a solvent control. A set of untreated control plants was alsoincluded for comparison. Preemergence and post-emergence treated plantsand controls were maintained in a greenhouse for sixteen days, then alltreated plants were compared with their respective controls and ratedvisually for response to treatment. Several of the compounds tested wereessentially innocuous to wheat but, at the same rate of application,provided effective weed control.

The following rating system was used:

O=no effect;

10=maximum effect;

C=chlorosis or necrosis;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

S=albinism;

U=increased chlorophyl;

X=axillary stimulation; and

6Y=abscised buds or flowers.

The test data are summarized in Table A.

                                      TABLE A                                     __________________________________________________________________________             Cmpd. 1                                                                             Cmpd. 2                                                                             Cmpd. 3                                                                             Cmpd. 4                                                                             Cmpd. 5                                                                             Cmpd. 6                                                                             Cmpd. 7                                                                             Cmpd.                                                                               Cmpd. 9              Rate kg/ha                                                                             2     2     2     2     2     2     0.05  0.05  0.05                 __________________________________________________________________________    POST-EMERGENCE                                                                Bush bean                                                                              1H,5G 4S,8G,6Y                                                                            6C,9G,6Y                                                                            6C,9G,6Y                                                                            5C,9G,6Y                                                                            1C,2G 5C,9G,6Y                                                                            6C,9G,6Y                                                                            5C,9G,6Y             Cotton   5C,9G 3C,3H,8G                                                                            5C,9G 5C,9G 6C,9G 2C,3H 4C,9G 5C,9G 6C,9G                Morningglory                                                                           1C,4G 1C    3C,9G 4C,9G 2C,6G 1C    10C   10C   4C,9G                Cocklebur                                                                              3C,7H 2C,7H 5C,9G 9C    5C,9G 3C,6H 10C   10C   6U,9G                Sicklepod                                                                              2C    2C    4C    4C    1C,2G 0     4C,6G 4C,8G 10C                  Nutsedge 2C,9G 2C,5G,5X                                                                            9G    2C,9G 1C,9G 2G    2C,8G 2C,9G 3C,9G                Crabgrass                                                                              6G    2C    2C,9G 1C,2G 2C,8G 1C,3G 2C,6G 2C,9G 4C,9G                Barnyardgrass                                                                          9H    1C    3C,9H 2C,5H 2C,8H 0     5C,9H 5C,9H 6C,9G                Wild Oats                                                                              0     0     2C,8G,5X                                                                            0     2C,6G 0     4C,9G 5C,9G 5C,9H                Wheat    0     0     3C,9G 2G    3C,9G 0     3U,9G 4C,9G 4C,9G                Corn     0     1C,3G 2U,9G 2C,9H 2C,9G 3C,7G 5U,9G 5U,9G 4C,7H                Soybean  1C,3G 1C,1H 4C,8G 4C,8G 2C,4H 2C,5G 6C,9G 5C,9G 10C                  Rice     2C,9G 0     5C,9G 5G    3C,9G 2C,7G 5C,9G 5C,9G 5C,9G                Sorghum  2C,7G 1C,4G 1C,9G 3C,8H 2C,9G 2C,9G 3C,9G 5C,9H 5C,9G                Sugar beet                       --    --    3C,9H 9C    9C                   __________________________________________________________________________             Cmpd. 10                                                                            Cmpd. 11                                                                            Cmpd. 12                                                                            Cmpd. 13                                                                            Cmpd. 14                                                                            Cmpd. 15                                                                            Cmpd. 16                                                                            Cmpd.                                                                               Cmpd. 18             Rate kg/ha                                                                             0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05                 __________________________________________________________________________    POST-EMERGENCE                                                                Bush bean                                                                              6C,9G,6Y                                                                            5C,9G,6Y                                                                            5C,9G,6Y                                                                            6C,9G,6Y                                                                            5C,9G,6Y                                                                            5C,9G,6Y                                                                            5C,9G,6Y                                                                            5C,8G,6Y                                                                            5S,9G,6Y             Cotton   4C,8G 5C,9G 0     2C,3G 2C,5G 3C,6G 2C,5G 3C,5G 4C,4H,8G             Sorghum  2C,9G 9G    2C,9G 2C,9G 9G    1C,9G 0     2C,8H 3C,9H                Corn     2U,9G 1U,9H 2C,9G 2C,9G 2C,9G 2C,9G 0     2C,6H 3C,8H                Soybean  9C    4C,8G 5C,9H 5C,9G 9C    9C    9C    4C,9G 3C,9G                Wheat    2C,9G 1C    7G    2C,7G 0     1C,6G 0     1H    1C                   Wild Oats                                                                              2C,9G 1C,5G 2C,9G 2C,7G 0     1C,6G 0     1H    2C                   Rice     9C    9C    6C,9G 5C,9G 5C,9G 6C,9G 0     2C,8G 2C,8G                Barnyardgrass                                                                          5C,9H 2C,9H 5C,9H 5C,8H 5C,9H 2C,9H 1H    2C,6H 5C,9H                Crabgrass                                                                              2C,8G 1C,3G 2C,5G 2C,4G 1C,6G 2C,6G 0     1C    5G                   Morningglory                                                                           5C,8H 10C   5G    3C,5G 2C,7G 2C,8G 5C,9G 5C,9G 3C,8G                Cocklebur                                                                              10C   10C   2C,8H 3C,9H 3C,8H 3C,8H 4G    2C,5G 2C,8H                Sicklepod                                                                              3C,8H 3C,5H 2C,5G 3C,6G 3C,9H 2C,6G 2C,8H 3C    2C,4G                Nutsedge 3C,8G 3G    2C,7G 5G    9G    1C,8G 5G    2C,6G 3C,7G                Sugar beet                                                                             9C    9C    2C,7H 10C   5C,9C 2C,9H 4C,9G --    --                   __________________________________________________________________________                                                   Cmpd. 19                                                                            Cmpd.                                                                              Cmpd. 21                                                  Rate kg/ha                                                                             0.05  0.05 0.05                __________________________________________________________________________                                          POST-EMERGENCE                                                                Bush bean                                                                              5C,9G,6Y                                                                            9C   9C                                                        Cotton   6C,9G 6C,9G                                                                              3C,9G                                                     Sorghum  9H    2G   2C                                                        Corn     2C,9G 2G   0                                                         Soybean  3C,9G 5C,9G                                                                              5C,9G                                                     Wheat    3G    0    0                                                         Wild Oats                                                                              3G    0    0                                                         Rice     2C,7G 0    0                                                         Barnyardgrass                                                                          9C    2H   0                                                         Crabgrass                                                                              2C,4G 0    2C                                                        Morningglory                                                                           5C,9H 10C  9C                                                        Cocklebur                                                                              5C,9G 9C   10C                                                       Sicklepod                                                                              5C,8H 4C,5G                                                                              3C,4H                                                     Nutsedge 2C,8G 5G   0                                                         Sugar beet                                                                             --    --   --                  __________________________________________________________________________             Cmpd. 1                                                                             Cmpd. 2                                                                             Cmpd. 3                                                                             Cmpd. 4                                                                             Cmpd. 5                                                                             Cmpd. 6                                                                             Cmpd. 7                                                                             Cmpd.                                                                               Cmpd. 9              Rate kg/ha                                                                             2     2     2     2     2     2     0.05  0.05  0.05                 __________________________________________________________________________    PRE-EMERGENCE                                                                 Morningglory                                                                           1C    2C    8G    8G    8G    1C,3G 5C,9G 9G    5C,9H                Cocklebur                                                                              8H    9H    --    9H    9H    9H    9H    9H    2C,9H                Sicklepod                                                                              1C    2C    9C    2C,7H 1C,5G 2C    9G    9G    9H                   Nutsedge 9G    10E   10E   10E   10E   9G    9G    10E   1C,9G                Crabgrass                                                                              2C    3C    2C,6G 2C    3C    0     2G    3C,6G 3C,9G                Barnyardgrass                                                                          5G    3C    3C,8H 5C    3C,6H 3C    2C,9H 5C,9H 10E                  Wild Oats                                                                              2G    2G    3C,9G 1C,6G 2C,9H 2C,8G 2C,9G 5C,9G 5C,9H                Wheat    2G    2G    3C,9G 4G    4C,9H 5G    2C,9G 4C,9G 2C,9G                Corn     2C,6G 2C,8G 9G    2U,9G 10E   2C,8G 9G    4C,9G 9G                   Soybean  0     1C,1H 5H    7H    8H    1C    2C,5H 9H    --                   Rice     3C,7H 2C,3G 10E   2C,8G 10E   9H    10E   10E   9G                   Sorghum  2C,7G 2C,7G 5C,9H 2C,9H 10E   3C,9G 5C,9H 5C,9H 10E                  Sugar beet                                   9G    10E   10E                  __________________________________________________________________________             Cmpd. 10                                                                            Cmpd. 11                                                                            Cmpd. 12                                                                            Cmpd. 13                                                                            Cmpd. 14                                                                            Cmpd. 15                                                                            Cmpd. 16                                                                            Cmpd.                                                                               Cmpd. 18             Rate kg/ha                                                                             0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05                 __________________________________________________________________________    PRE-EMERGENCE                                                                 Sorghum  5C,9H 5C,9H 3C,9H 5C,9G 5C,9H 9H    2G    4G    3C,9H                Corn     2C,9G 2C,9H 3C,9G 3C,9H 2C,9G 9G    1C,6G 3C,6G 2C,8H                Soybean  9H    2C,5H 5H    8H    8H    9H    8H    1C    3C,8H                Wheat    2C,9G 0     2C,9G 2C,9G 1C,6G 2C,9G 0     5G    8G                   Wild Oats                                                                              4C,9G 5H    3C,7G 3C,8G 1C,3G 3C,8G 2C    2C,4G 2C,8G                Rice     10E   10E   2C,9H 10E   9H    9H    2G    0     3C,6G                Barnyardgrass                                                                          5C,9H 2C,7H 5C,9H 5C,9H 5C,9H 5C,9H 2C    3G    3C,9H                Crabgrass                                                                              2C,8G 0     2C    2C,4G 2C,6G 4C,8G 0     3G    2C,5G                Morningglory                                                                           9C    9C    8G    9G    7G    8G    9G    5G    8H                   Cocklebur                                                                              --    9H    9H    9H    9H    9H    9H    8H    9H                   Sicklepod                                                                              9G    3C,9G 9G    8G    9G    9G    8G    8G    9G                   Nutsedge 5C,9G 0     2C,9G 10E   10E   10E   5G    2G    8G                   Sugar beet                                                                             10E   10E   9G    10E   10E   10E   10E   --    --                   __________________________________________________________________________                                                   Cmpd. 19                                                                            Cmpd.                                                                              Cmpd. 21                                                  Rate kg/ha                                                                             0.05  0.05 0.05                __________________________________________________________________________                                          PRE-EMERGENCE                                                                 Sorghum  4C,9H 2G   0                                                         Corn     9G    1C,4G                                                                              0                                                         Soybean  9H    9H   0                                                         Wheat    7G    0    0                                                         Wild Oats                                                                              2C,8G 0    0                                                         Rice     10E   1C,4G                                                                              0                                                         Barnyardgrass                                                                          3C,9H 2G   0                                                         Crabgrass                                                                              3C,8G 2G   2G                                                        Morningglory                                                                           9G    9G   8G                                                        Cocklebur                                                                              9H    9H   9H                                                        Sicklepod                                                                              9G    9G   9G                                                        Nutsedge 10E   3G   0                                                         Sugar beet                                                                             --    --   --                  __________________________________________________________________________

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsingtonsilt loam or Woodstown sandy loam soil. One pan was planted with corn,sorghum, Kentucky bluegrass and several grass weeds. The other pan wasplanted with cotton, soybeans, purple nutsedge (Cyperus rotundus), andseveral broadleaf weeds. The following grassy and broadleaf weeds wereplanted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur(Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory(Ipomoea hederacea), sicklepod (Cassia obtusifolia), teaweed (Sidaspinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Daturastramonium). A 12.5 cm diameter plastic pot was also filled withprepared soil and planted with rice and wheat. Another 12.5 cm pot asplanted with sugar beets. The above four containers were treatedpre-emergence with several test compounds within the scope of theinvention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B.

                                      TABLE B                                     __________________________________________________________________________    PRE-EMERGENCE ON                                                              FALLSINGTON SILT LOAM SOIL                                                    __________________________________________________________________________            Compound 3                                                                            Compound 7                                                                            Compound 8                                                                            Compound 9                                                                           Compound 10                                                                           Compound                                                                              Compound 12            Rate kg/ha                                                                            0.03                                                                              0.12                                                                              0.12                                                                              0.03                                                                              0.12                                                                              0.03                                                                              0.12                                                                              0.03                                                                             0.12                                                                              0.03                                                                              0.12                                                                              0.03                                                                              0.06                                                                              0.015              __________________________________________________________________________    Crabgrass                                                                             3G  4G  8G  7G  9G  8G  9G  8G 9G  8G  5G  2G  0   0                  Barnyardgrass                                                                         4G,2C                                                                             5G,3C                                                                             9G,9C                                                                             9G  10C 9G,9C                                                                             9G,9C                                                                             9G 10C 9G,9C                                                                             8G,5C                                                                             6G  0   0                  Sorghum 4G  5G  10C 10C 10C 10C 10C 10C                                                                              10C 10C 10C 9G  7G  6G                 Wild Oats                                                                             0   3G  9G  9G  9G  9G  9G  9G 9G  9G  8G  7G  4G  2G                 Johnsongrass                                                                          6G  5G  9G  9G  9G  9G  9G  9G 9G  9G  8G  8G  4G  2G                 Dallisgrass                                                                           3G  3G  9G  9G  9G  9G  9G  9G 9G  9G  6G  3G  2G  0                  Giant foxtail                                                                         4G  4G  8G  2G  10C 8G  10C 9G 9G  7G  4G  2G  0   0                  Ky. bluegrass                                                                         3G  6G  10C 9G  10C 9G  10C 9G 10C 9G  4G  2G  6G  4G                 Cheatgrass                                                                            0   3G  10C 10C 10C 10C 10C 10C                                                                              10C 10C 8G  5G  7G  5G                 Sugar beets                                                                           2G  5G  10C 9G  10C 10C 10C 10C                                                                              10C 10C 10C 10C 5G  4G                 Corn    4G  3G  10C 9G  10C 9G  10C 7G 10C 9G  9G  5G,3H                                                                             0   0                  Mustard 4G  6G,5H                                                                             10C 10C 10C 10C 10C 10C                                                                              10C 10C 10C 10C 9G  8G                 Cocklebur                                                                             2G  0   9G  8G  10C 9G  10C 9G 9G  9G  9G  8G  2G  2G                 Pigweed 0   8G,9C                                                                             --  --  --  --  --  -- --  --  --  --  --  --                 Nutsedge                                                                              0   0   10C 9G  10C 10C 10C 10C                                                                              10C 10C 9G  8G  0   0                  Cotton  0   2G  9G  8G  9G  9G  9G  9G 9G  9G  9G  8G  2G  2G                 Morningglory                                                                          0   0   9G  8G  9G  9G  9G  8G 9G  9G  9G  8G  3G  0                  Sicklepod                                                                             0   3G  9G  8G  9G  9G  9G  9G 9G  9G  9G  8G  0   0                  Teaweed 0   3G  9G  9G  9G  9G  9G  9G 9G  9G  9G  8G  0   0                  Velvetleaf                                                                            0   3G  9G  9G  9G  9G  9G  9G 9G  9G  9G  8G  0   0                  Jimsonweed                                                                            0   2G  9G  9G  9G,9C                                                                             9G  9G,9C                                                                             9G 9G,9C                                                                             9G  9G  8G  2G  0                  Soybean 3G  5G  8G,7H                                                                             6G,5H                                                                             9G  9G  9G  9G 9G  9G  7G,7H                                                                             2G,2C                                                                             0   0                  Rice    6G  7G  10C 10C 10C 10C 10C 10C                                                                              10C 10C 10C 10C 9G  7G                 Wheat   2G  4G  10C 8G  10C 9G  7G  4G 9G  8G  4G  2G  5G  5G                 __________________________________________________________________________                                      Compound 13                                                                          Compound 14                                                                          Compound                                                                             Compound 16                                      Rate kg/ha                                                                            0.06                                                                              0.015                                                                            0.06                                                                              0.015                                                                            0.06                                                                              0.015                                                                            0.12                                                                              0.03               __________________________________________________________________________                              Crabgrass                                                                             2G  0  3G  0  5G  2G 0   0                                            Barnyardgrass                                                                         7G  4G 3G  5G 6G  4G 5G  3G                                           Sorghum 9G  4G 10C 2G 9G  7G 4G  2G                                           Wild Oats                                                                             6G  0  3G  2G 5G  4G 4G  2G                                           Johnsongrass                                                                          8G  2G 3G  2G 3G  2G 2G  0                                            Dallisgrass                                                                           2G  0  2G  0  6G  2G 5G  2G                                           Giant foxtail                                                                         8G  0  2G  2G 3G  0  0   0                                            Ky. bluegrass                                                                         7G  3G 6G  3G 9G  7G 3G  3G                                           Cheatgrass                                                                            8G  4G 9G  8G 8G  7G 5G  4G                                           Sugar beets                                                                           7G  3G 5G  4G 6G  4G 10C 9G                                           Corn    7G,7H                                                                             3G 4G  3G 5G  4G 4G  3G                                           Mustard 10C 9G 10C 9G 9C,9G                                                                             9G 10C 9G,9C                                        Cocklebur                                                                             2G  0  0   0  4G  0  7G  5G                                           Pigweed --  -- --  -- --  -- --  --                                           Nutsedge                                                                              4G  2G 3G  2G 3G  2G 7G  5G                                           Cotton  4G  0  2G  0  3G  2G 7G  4G                                           Morningglory                                                                          3G  3G 4G  3G 4G  4G 8G  5G                                           Sicklepod                                                                             4G  4G 7G  2G 2G  0  9G  8G                                           Teaweed 6G  0  0   0  2G  0  3G  0                                            Velvetleaf                                                                            6G  0  0   0  5G  2G 2G  0                                            Jimsonweed                                                                            7G  0  5G  4G 4G  3G 5G  4G                                           Soybean 6G,5H                                                                             0  2G  0  2G  2G 6G,5H                                                                             5G,3H                                        Rice    9G  7G 8G  8G 8G  8G 6G  6G                                           Wheat   6G  6G 3G  3G 5G  3G 2G  2G                 __________________________________________________________________________

Test C

The test chemicals, dissolved in a non-phytotoxic solvent, were appliedin an overall spray to the foliage and surrounding soil of selectedplant species. One day after treatment, plants were observed for rapidburn injury. Approximately fourteen days after treatment, all specieswere visually compared to untreated controls and rated for response totreatment. The rating system was as described previously for Test A. Thedata are presented in Table C.

All plant species were seeded in Woodstown sandy loam or Fallsingtonsilt loam soil and grown in a greenhouse. The following species weregrown in soil contained in plastic pots (25 cm diameter by 13 cm deep):soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf(Abutilon theophrasti), sesbania (Sesbania exaltata), sicklepod (Cassiaobtusifolia), morningglory (Ipomoea hederacea), jimsonweed (Daturastramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitariasp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloacrusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua).The following species were grown in soil in a paper cup (12 cm diameterby 13 cm deep): sunflower, sugar beets, and rape. All plants weresprayed approximately 14 days after planting. Additional plant speciessuch as johnsongrass and bindweed, are sometimes added to this standardtest in order to evaluate unusual selectivity.

Compound Nos. 20 and 21 exhibit selectivity in post-emergence control ofweeds in corn and wheat.

                                      TABLE C                                     __________________________________________________________________________    Over-the-Top Soil/Foliage Treatment                                           __________________________________________________________________________             Compound 3                                                                            Compound 5                                                                              Compound 7  Compound 8  Compound 9                 Rate kg/ha                                                                             0.06                                                                              0.25                                                                              0.06 0.25 0.06                                                                              0.015                                                                             0.004                                                                             0.06                                                                              0.015                                                                             0.004                                                                             0.06                                                                              0.015                                                                             0.004              __________________________________________________________________________    Soybeans 3G,2C                                                                             5G,2C                                                                             6G,2C                                                                              9G,5C                                                                              10C 7G,2C                                                                             2G  8G,6C                                                                             6C,7G                                                                             6G,6C                                                                             10C 9C  8G,7C              Velvetleaf                                                                             0   6G,1C                                                                             0    4G   7G,4C                                                                             6G  3G  9G  4C,6G                                                                             2C,7G                                                                             10C 9C  9C                 Sesbania 4G  5G  6G,2C                                                                              6G,2C                                                                              10C 10C 7G  9C  10C 9C  10C 10C 8G                 Sicklepod                                                                              1C  2C  5G   0    8G  6G  2G  6G  3G  2G  4G  5G  8G                 Cotton   6G,3C                                                                             8G,5C                                                                             1G   5G,1C                                                                              8G  6G  3G  10C 9G  9G  10C 9G  9G                 Morningglory                                                                           1G,2C                                                                             3G,2C                                                                             2C   4G,2C                                                                              --  --  --  5G,3C                                                                             3G,2C                                                                             4G,2C                                                                             3C,8G                                                                             1G,1C                                                                             4C,4G              Alfalfa  0   1G  0    2G                                                      Jimsonweed                                                                             1C  --  0    1C   8G  6G  4G  7C,8G                                                                             8G,7C                                                                             7G  8G  9G  6G                 Cocklebur                                                                              6G,2C                                                                             5G,2C                                                                             10G,2C                                                                             10G,5C                                                                             8G  6G  3G  8G  9G  7G  9G  7G  10C                Corn     3G  5G,3C                                                                             8G,5H                                                                              6G,5H                                                                              7G,9C                                                                             5C,7G                                                                             2G  7G,8C                                                                             4G,4C                                                                             3G,1C                                                                             3C,5G                                                                             4G,1C                                                                             4G,3H              Crabgrass                                                                              1G  1G  0    0    7G  5G  8G  9G  7G  1G  7G  3G  0                  Rice     5G  7G  6G   5G   8G,2C                                                                             7G  4G  6G,4C                                                                             4C,4G                                                                             4G  6C,4G                                                                             5G,5C                                                                             3G                 Nutsedge 4G  8G,4C                                                                             7G,3C                                                                              0    3G  2G  --  10C 8C  3G  8G,8C                                                                             7G,8C                                                                             6G,4C              Barnyardgrass                                                                          7G,2C                                                                             6G,1C                                                                             2C   1C   6G  1C,2G                                                                             1G  7G  4G  5G  6G,4C                                                                             5G,5C                                                                             6G                 Wheat    1G  1G  6G   2C   9G  7G  5G  8G  5G  4G  5G  4G  3G                 Giant foxtail                                                                          7G  5G  1G   0    --  --  --  9G  7G  1G  8G  7G  4G                 Wild Oats                                                                              4G  5G  4G   3G   8G  7G  --  6G  6G  2G  8G  7G  1G                 Sorghum  7G,1C                                                                             7G,1C                                                                             7G   5G,4C                                                                              7G  7G  6G  6G  5G  4G  10C 7G,7C                                                                             7G                 Sunflower                  10C 2C,8G                                                                             3G  10C 10C 10C 10C 10C 10C                Rape                       5C,4G                                                                             2C,3G                                                                             1C,3G                                                                             9G  8G  6G,3C                                                                             10C 9C  7G                 Johnsongrass               9G  7G  9G  10C 7C,8G                                                                             7G  10C 8G,7C                                                                             7G,7C              Sugar beets                9C  6G  2C,3G                                                                             5G  10C 8C  5C  4G  3G                 Bindweed                   5G  2G  1C  2G  0   0   0   0   0                  __________________________________________________________________________             Compound 11                                                                            Compound 12                                                                            Compound 13                                                                            Compound 14                                                                            Compound 15                                                                            Compound 16             Rate kg/ha                                                                             0.06                                                                              0.015                                                                              0.06                                                                              0.015                                                                              0.06                                                                              0.015                                                                              0.06                                                                              0.015                                                                              0.06                                                                              0.015                                                                              0.06                                                                              0.015               __________________________________________________________________________    Soybeans 10C 9C   8C,4G                                                                             7G,2C                                                                              8C,7G                                                                             8C   9C  8G   10C 10C  10C 9C                  Velvetleaf                                                                             8G  7G   7G  3G   3G  1C,2G                                                                              4G  3G   8G  3G   6G  2G                  Sesbania 8G,9C                                                                             8G,7C                                                                              8G,4C                                                                             7C,3G                                                                              8G,4C                                                                             1C,7G                                                                              10C 7G   10C 8G   10C 10C                 Sicklepod                                                                              6G  4G   8G  6G   2C,5G                                                                             8G   5G  2G   8G  4G   8G  5G                  Cotton   9G,9C                                                                             --   7G  --   8G  7G,4C                                                                              8G  6G   4G,7C                                                                             6G   8G  3G                  Morningglory                                                                           9G  9G,8C                                                                              --  3G   9G  9G   9C  4G   8G  5G   4G,1C                                                                             1G                  Jimsonweed                                                                             9G  8G   8G  9G   --  9G   --  --   4G,3C                                                                             8G   9G  6G                  Cocklebur                                                                              10C 9G   7G  --   7G,2C                                                                             7G   9C  3G   10C 7G   7G  2G                  Corn     8G  6G,4C                                                                              7G  4G   5C,6G                                                                             7G   10C 7G,5C                                                                              7G,4C                                                                             6G   1H,4G                                                                             1G                  Crabgrass                                                                              2G  0    5G  6G   6G  1G   7G  7G   5G  2G   3G  1G                  Rice     6G,4C                                                                             4G   5G,4C                                                                             6G,3C                                                                              4G  3G   6G,4C                                                                             4G   6G,5C                                                                             4G,3C                                                                              2G  0                   Nutsedge 0   0    3G  0    0   0    5G  4G   4G,3C                                                                             3G,3C                                                                              0   0                   Barnyardgrass                                                                          6G  5G,3C                                                                              9G,7C                                                                             7G,4C                                                                              10C 7C,6G                                                                              10C 10C  9G  8G   3G  1G                  Wheat    5G  5G   7G  4G   5G  4G   5G  4G   8G  2G   4G,1C                                                                             1G                  Giant foxtail                                                                          4G  0    6G  5G   3C,4G                                                                             3G   8G  5G   3C,8G                                                                             6G,1C                                                                              2G  0                   Wild Oats                                                                              7G  5G   8G  3G   9G  8G   6G  6G   3G  2G   3G,2C                                                                             2C,1G               Sorghum  8G  8G   8G  8G   8G  9G   8G  8G   8G  8G   4G  1G                  Sunflower                                                                              10C 10C  8G  2G   10C 2C,6G                                                                              10C 8G   10C --   7G  5G                  Rape     9G  8G   8G  7G   9G  8G   6G  7G   8G  7G   10C 10C                 Johnsongrass                                                                           1G  0    7C,8G                                                                             2G   5G,4C                                                                             1G   7G  4G   9G  2G   0   0                   Sugar beets                                                                            7C,8G                                                                             8G,5C                                                                              6G  5G   7G  8C   6G  6G   10C 3G   6C,5G                                                                             4G                  Bindweed 4G  3G   6G  2G   0   0    2G  0    5G  2G   0   0                   __________________________________________________________________________                     Compound 17                                                                              Compound 18 Compound 19                                                                           Compound                                                                              Compound 21                    Rate kg/ha                                                                            0.06                                                                              0.015                                                                             0.004                                                                            0.06                                                                              0.015                                                                             0.004                                                                             0.015                                                                             0.004                                                                             0.06                                                                              0.015                                                                             0.06                                                                             0.015              __________________________________________________________________________             Soybeans                                                                              9C  6C,6G                                                                             3C 7C,6G                                                                             8C  5G,7C                                                                             9C  4G,5C                                                                             9C  10C 10C                                                                              10C                         Velvetleaf                                                                            4G  3G  4G 5G  3C,6G                                                                             3G  3G  3G  3G  3G  3G 2G                          Sesbania                                                                              4C,5G                                                                             4G  3G 9G  7G  3G  7C,6G                                                                             7G,4C                                                                             10C 10C 10C                                                                              10C                         Sicklepod                                                                             9G  6G  4G 6G  3G  2G  2G  0   8G  --  8G 6G                          Cotton  8G  7G  3G 9C  8G  6G  5G  4G  8G  8G  9C 7G                          Morningglory                                                                          7G  3G  0  8G  9C  5G  3G  0   10C 10C 9C 2C,4G                       Jimsonweed                                                                            0   0   0  9G  4G  3G  6G  1G  7G  4G  6G 4G                          Cocklebur                                                                             8G  3G  4G 3G  5G  4G  2G  1G  10C 10C 9G 4G                          Corn    0   0   0  4H,5G                                                                             4G  0   0   0   0   0   0  0                           Crabgrass                                                                             0   0   0  1G  0   0   2G  0   0   0   0  0                           Rice    3G  0   0  2G  0   0   0   0   0   0   1G 0                           Nutsedge                                                                              0   0   0  0   0   0   3C  0   0   0   2G 0                           Barnyardgrass                                                                         0   0   0  2G  3G  0   0   0   0   0   0  0                           Wheat   0   0   0  1G  0   0   0   0   0   0   0  0                           Giant foxtail                                                                         0   0   0  2G  0   0   0   0   0   0   1G 0                           Wild Oats                                                                             0   0   0  1G  1G  0   0   0   1G  0   0  0                           Sorghum 2G  0   0  7G  4G  0   5G  2G  0   0   0  0                           Sunflower                                                                             5G  3G  4G 3G  5G  3G  3G  2G  10C 10C 9G 9G                          Rape    6G  5G  5G 8G  6G  4G  9C  9G  10C 10C 10C                                                                              7G,9C                       Johnsongrass                                                                          0   0   0  1G  0   0   0   0   0   0   2G 0                           Sugar beets                                                                           2G  0   0  9G  3G  9G  4G  0   10C 10C 8G 5G                          Bindweed                                                                              4G  0   0  3G  3G  0   8G  2G  4G  0   0  0                  __________________________________________________________________________

Test D

Two plastic pans lined with polyethylene liners were filled withprepared Woodstown sandy loam soil. One pan was planted with seeds ofwheat (Triticum aestivum), barley (Hordeum vulgare), wild oats (Avenafatua), cheatgrass (Bromus secalinus), blackgrass (Alopecurusmyosuroides), annual bluegrass (Poa annua), green foxtail (Setariaviridis), Italian ryegrass (Lolium multiflorum) and rapeseed (Brassicanapus). The other pan was planted with seeds of Russian thistle (Salsolakali), cleavers (Galium aparine), speedwell (Veronica persica), kochia(Kochia scoparia), shepherd's purse (Capsella bursa-pastoris),Matricaria inodora, black nightshade (Solanum nigrum), wild buckwheat(Polygonum convolvulus) and sugar beets (Beta vulgaris). Species whichsometimes are included in this test are tansy mustard (Descurainapinnata), tumble mustard (Sisymbrium altissium), ripgut brome (Bromusrigidus), quackgrass (Agropyron repens), downy brome (Bromus tectorum)and yellow rocket (Barbarea vulgaris). The above two pans were treatedpre-emergence. At the same time two pans in which the above plantspecies were already growing were treated post-emergence. Plant heightsat the time of treatment ranged from 1-20 cm depending on plant species.

The compounds applied were diluted with a nonphytotoxic solvent andsprayed over-the-top of the pans. An untreated control and a solventalone control were included for comparison. All treatments weremaintained in the greenhouse for 19-22 days at which time the treatmentswere compared to the controls and the effects visually rated. Therecorded data are presented in Table D. Some of the compounds testedexhibit selectivity while controlling weeds in cereal crops, such aswheat and barley.

                                      TABLE D                                     __________________________________________________________________________               Compound 9       Compound 11       Compound 11                                Pre-Emergence                                                                         Post-Emergence                                                                         Pre-Emergence                                                                         Post-Emergence                                                                          Pre-Emergence                                                                         Post-Emergence          Rate kg/ha 0.015                                                                             0.004                                                                             0.015                                                                              0.004                                                                             0.06                                                                              0.015                                                                             0.06 0.015                                                                              0.015                                                                             0.004                                                                             0.015                                                                              0.004              __________________________________________________________________________    wheat      5G  2G  5G   5G  1G  0   2G   0    0   0   0    0                  barley     9G  7G  9G   5G  4G  0   2G   0    0   0   0    0                  wild oats  7G  6G  6G   4G  2G,8G                                                                             5G  6G   2G   0   0   0    0                  cheatgrass 9G  8G  7G   8G  6G  0   0    0    0   0   0    0                  blackgrass 8C,9G                                                                             8G  10C  8C,9G                                                                             2C,8G                                                                             6G  8G   2C,5G                                                                              5G  4G  5G   0                  annual bluegrass                                                                         4C,9G                                                                             8G  10C  10C 8G  7G  8G   4G   6G  4G  4G   0                  green foxtail                                                                            8G  0   9G   8G  3G  3G  3G   3G   3G  2G  3G   0                  Italian ryegrass                                                                         8G  7G  3C,8G                                                                              7G  2C,8G                                                                             6G  5G   0    1C,5G                                                                             3G  2G   0                  rapeseed   10C 9G  10C  10C 9G  9G  9G   --   9G  9G  10C  8G                 ripgut brome                                                                             --  --  --   --  8G  6G  7G   0    --  --  --   --                 Matricaria inodora                                                                       9G  9G  10C  10C 7C,9G                                                                             7G  6G   --   9G  5G  9C,9G                                                                              8C,8G              Galium aparine                                                                           8G  8G  10C  10C 3C,9G                                                                             7G  6G   --   7G  2G  10C  9C,9G              Russian thistle                                                                          0   3G  10C  8C  2C,8G                                                                             3G  0    0    2G  0   0    0                  shepherd's purse                                                                         10E 10E 10C  10C 9C,9G                                                                             8G  6G   --   10C 7G  10C  10C                kochia     8G  8G  9C,9G                                                                              9C,9G                                                                             8G  0   0    0    5G  0   5G   0                  black nightshade                                                                         7G  5G  7G   5G  6G  4G  2G   --   6G  2G  5G   0                  speedwell  4G  3G  3G   0   7G  2G  --   --   2G  2G  0    0                  wild buckwheat                                                                           4G  6G  10C  3G,8C                                                                             2C,8G                                                                             6G  0    --   2C,9G                                                                             7G  7G   3G                 sugar beets                                                                              8G  8G  10C  10C --  --  --   --   10C 9G  10C  8G                 tansy mustard                                                                            --  --  --   --  5C,9G                                                                             9G  8G   --   --  --  --   --                 tumble mustard                                                                           --  --  --   --  9C,9G                                                                             7G  0    0    --  --  --   --                 __________________________________________________________________________               Compound 14      Compound 15       Compound 20                                 Pre-Emergence                                                                        Post-Emergence                                                                         Pre-Emergence                                                                          Post-Emergence                                                                         Pre-Emergence                                                                         Post-Emergence          Rate kg/ha 0.015                                                                             0.06                                                                              0.015                                                                              0.06                                                                              0.015                                                                              0.06                                                                              0.015                                                                              0.06                                                                              0.06                                                                              0.015                                                                             0.06 0.015              __________________________________________________________________________    wheat      2G  4G  2G   2G  6G   7G  2G   5G  0   0   0    0                  barley     2G  5G  3G   4G  6G   7G  2G   6G  2G  0   0    0                  wild oats  3G  5G  2G   2G  5G   7G  2G   4G  3G  0   0    0                  downy brome                                                                              --  --  --   --  --   --  --   --  4G  0   0    0                  cheatgrass 3G  6G  2G   4G  2C,8G                                                                              10C 0    6G  0   0   0    0                  blackgrass 6G  8G  4G   6G  2C,8G                                                                              3C,8G                                                                             4G   2C,8G                                                                             4G  4G  0    0                  annual bluegrass                                                                         6G  2C,8G                                                                             5G   6G  2C,9G                                                                              3C,9G                                                                             6G   2C,8G                                                                             4G  3G  2G   0                  green foxtail                                                                            0   5G  6G   8G  6G   2C,9G                                                                             5G   7G  2G  0   3G   0                  quackgrass --  --  --   --  --   --  --   --  3G  0   0    0                  Italian ryegrass                                                                         5G  2C,7G                                                                             2G   4G  2C,9G                                                                              2C,9G                                                                             3G   5G  4G  3G  0    0                  ripgut brome                                                                             --  --  --   --  --   --  --   --  2G  0   0    0                  Russian thistle                                                                          2C,2G                                                                             2C,3G                                                                             0    2C  2C,5G                                                                              2C,6G                                                                             0    2G  0   0   0    0                  tansy mustard                                                                            --  --  6G   2C,8G                                                                             --   --  4G   8C  10C 9G  10C  10C                Galium aparine                                                                           --  --  0    2C,4G                                                                             5G   --  2G   0   5G  5G  3G   4G                 tumble mustard                                                                           10C 9G  4G   10C 10C  10C 4G   10C 9G  8G  10C  8G                 kochia     6G  8G  0    7C  6G   10C 0    7G  8G  6G  0    0                  shepherd's purse                                                                         9G  9C,9G                                                                             4G   3C,8G                                                                             9G   10C 3G   2C,8G                                                                             10C 9G  10C  10C                Matricaria inodora                                                                       9G  9G  3G   3C,8G                                                                             9G   9G  2G   6G  9G  9G  9C   8C                 black nightshade                                                                         3G  6G  0    5G  3G   6G  0    0   5G  5G  0    0                  yellow rocket                                                                            9G  9G  0    3G  9G   9G  4G   6G  9G  8G  10C  10C                rapeseed   8G  9C,9G                                                                             7G   10C 9C   10C 5G   8G  9G  7G  10C  10C                wild buckwheat                                                                           7G  7G  0    2G  7G   7G  5G   7G  5G  7G  6G   3G                 Veronica persica                                                                         7C,9G                                                                             10C --   --  9G   9C,9G                                                                             --   --                                  __________________________________________________________________________

What is claimed is:
 1. A compound of the formula: ##STR122## where Q is##STR123## where W is O or S;W' is O or S; R₁ is H, F, Cl, Br, CH₃, CF₃or OCH₃ ; R₁₂ is H or CH₃ ; R₁₂ ' is H or CH₃ ; R₁₃ is H or CH₃ ; R₁₈ isH or CH₃ ; R₁₉ is H or CH₃ ; R₂₀ is H or CH₃ ; R₂₁ is H or CH₃ ; R₂₂ isH or CH₃ ; R₂₃ is H or CH₃ ; A is ##STR124## X₁ is CH₃, OCH₃ or C₁ ; Gis Oand their agriculturally suitable salts; provided that (1) when W isS, then R₁₃ is H; the total number of carbon atoms in R₁₂, R₁₂ ', R₁₈,R₁₉, R₂₀, R₂₁, R₂₂ and R₂₃ is less than or equal to
 4. 2. Compounds ofclaim 1 where R₁ and R₁₃ are H.
 3. Compounds of claim 2 where Q is##STR125##
 4. Compounds of claim 2 where Q is ##STR126##
 5. Compounds ofclaim 2 where Q is ##STR127##
 6. Compounds of claim 2 where Q is##STR128##
 7. Compounds of claim 2 where Q is ##STR129##
 8. Compounds ofclaim 2 where Q ##STR130##
 9. Compounds of claim 2 where Q ##STR131##10. Compounds of claim 2 where Q ##STR132##
 11. A composition suitablefor controlling the growth of undesired vegetation which comprises aneffective amount of a compound of claim 1 and at least one of thefollowing: surfactant, solid or liquid inert diluent.
 12. A compositionsuitable for controlling the growth of undesired vegetation whichcomprises an effective amount of a compound of claim 2 and at least oneof the following: surfactant, solid or liquid inert diluent.
 13. Amethod for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 1. 14. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim 2.